Okay, Actually is a podcast for people who are working hard and starting to wonder if the problem is them. It's not.

Each episode, we dig into what's truly broken and figure out how to build a solution that can actually work.

In this episode, I'm joined by Jennifer D'Agostino, a fractional HR executive and someone who has been handed more broken hiring processes than she can count. We're talking about where hiring actually goes wrong — which is almost always before the first resume arrives. The job description, the backfill bias, the hiring manager who's too busy to engage, the culture fit that's really just a clone request. Jennifer has seen all of it, and she's direct about what it costs.

00:00 Hiring Clarity Gap

00:54 Meet Jen D'Agostino

02:07 Root Causes Beyond Search

05:36 Fixing Job Descriptions

09:35 Stop Cloning Past Stars

12:13 Neutral Review Market Data

15:18 Engaged Hiring Managers Win

17:27 Bias Culture Add

21:58 Three Questions Before Posting

26:38 Wrap Up & Key Takeaways

About Jennifer: Jennifer D'Agostino is a fractional HR executive with more than 20 years of VP-level experience in corporate HR, most recently as VP of HR and Talent Management at RTI International. She now partners directly with small business CEOs and COOs through her own practice, helping growing companies attract, develop, and retain the right people — starting with an honest assessment of what they actually need.

Connect with Jennifer:

LinkedIn

Purpose HR

Find me:

OkayDoak.com

[email protected]

At some point, most organizations decide to hire

2

their way out of a problem.

3

The role opens, the job description

goes out, and it's usually a version

4

of the last one, maybe with a few

new lines added by someone in comp.

5

And six months later, the wrong person

is in the seat, or the right person

6

left, or the role got redefined three

times and nobody told the recruiter.

7

And the assumption almost universally is

that something went wrong in the search.

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Wrong candidates, wrong

process, wrong hire.

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But what almost nobody asks is,

did we actually know what we were

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looking for before we started?

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Did we know what problem this

role was supposed to solve?

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Did we know what the team

needed versus what we lost?

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Did we write a job description that

reflected reality, or did we write a

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wish list and call it a job description?

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I'm Karen Doak, and this is OK Actually.

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If what I describe sounds familiar,

and I think it probably does for many

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of you, I want you to meet someone

who's been handed that exact mess from

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the HR side for twenty plus years.

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So Jen and I were introduced by a

mutual friend, hi Maria, when we both

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decided to build our own practices

instead of staying in corporate.

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And I knew I'd like her right away because

she called herself the queen of get shit

22

done, and that is what I'm all about.

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So I love anyone with a GSD attitude.

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Um, but beyond that, Jen D'Agostino has

spent more than 20 years inside corporate

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HR at the VP level, most recently as

VP of HR and talent management at RTI

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International, and has spent years

managing talent acquisition for large

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organizations and business units, and

hiring at just an incredibly high volume.

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Now she is a fractional HR executive

and expert who partners directly

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with small business CEOs and COOs,

which I love because it means that

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she's getting a lot closer to the

actual business problem, which is

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what we are here to talk about today.

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So welcome, Jen

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Jen: Thanks.

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Thanks for having me, Karen.

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It's great to be here.

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I'm looking forward to the conversation

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Karen Doak: Knowing that you spent

20-plus years inside corporate HR before

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going fractional, at, at what point

did you start noticing that hiring

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problems, uh, that you were being handed

weren't necessarily hiring problems,

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but maybe had other root causes?

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Jen: Oh, pretty early on in my

career, I think I learned that

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hiring problems are generally coming

from lots of different places.

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And, and when I think about what's

is at the root of hiring problems,

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you know, you have to look at why

someone has left the position, right?

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So there's that, which is that, you

know, this employee engagement kind

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of what's happening with that space.

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And maybe it's nothing.

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Maybe they just got a better offer

someplace, and so they took another

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job, but maybe there's a manager issue.

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And so if you're filling the same job

lots of times, that was always a red

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flag for the recruitment team of like,

oh, this is, this is a problem space

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that we're gonna try and fill, and no

candidate's probably gonna fix this,

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but we're just gonna keep filling

this, uh, you know, hole rather than

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dealing with the issue of the manager.,

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But then if it's, if it's nothing, if it's

totally innocent and someone's just taken

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another job and you have to backfill,

if the hiring manager is not paying

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attention, is not really tuned in to what

they're looking for, is not taking the

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time to think about what they need for

the future, it's just like an autopilot.

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That is often where we see

a lot of the challenges.

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, And they're busy, right?

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They don't wanna spend the time, , to

do this, but if they don't spend

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the time, they're gonna probably

have to do it two or three times.

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Karen Doak: From your standpoint, do you

think that, I mean, every time someone

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leaves, is that an opportunity to revisit

the role, the needs, the approach?

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Or that, that point you made about

just people being on autopilot

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suggests that, that that sort of

refresh or rethinking isn't happening

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Jen: Yeah, I think that when

a position comes open, there's

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two things that can happen.

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One, you can do autopilot, where

you're not thinking about how has

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the scope changed, how has the role

or the organization changed, or what

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is the demands of the company now

versus when you originally filled it.

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, Or you can have the opposite effect when

the hiring manager goes into, like, super

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deep analytical, "Oh, we have to rewrite

this, and we have to rethink everything."

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I think there's a middle ground somewhere

where it's like, okay, we need 80% of

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what we had in the previous person,

but the 20% that we need to redraft or

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rethink takes some actual, uh, intent

and thought to, to p- put through.

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, And so I think the recruiter's

responsibility, and sometimes

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recruiters don't feel like they have

this, , ability to say this, is to stop

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and think and to pause and to really

go into how, how is the job working?

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What would you have loved to see?

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What were some of the skills

that that person was missing?

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What are the competencies that

you wanna round out in your team?

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Having those conversations will make

for a better process all around.

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Karen Doak: Yeah, and I would imagine

that that kind of conversation

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also would lead to a better and

more specific job description.

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'Cause I think something I've certainly

noticed is I've read a lot of job

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descriptions that feel very ChatGPT or,

or prior to ChatGPT feel like they were

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copy and pasted from decades prior.

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so I think I'm, I'm wondering too

about just the, the role of the

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recruiter and the hiring manager

in getting to a place where there's

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a better, stronger job description

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Jen: Yeah.

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I think in this day and age right

now, we have such an opportunity

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to elevate our job descriptions and

really just change them dramatically.

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I think there was a bit of a movement,

um, maybe in the last two years around

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moving to more skills and actual tasks

based in the job description, and less

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core requirements or previous experience.

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That is one element that could be

changed, but really rather than it

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being something that's gonna qualify a

compensation model, which is typically

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how job descriptions are created

is from a compensation model, is

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What is the job actually doing,

and what does success look like

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for this person or for this role?

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, And then focusing on the skills

and the tasks rather than you

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have to have this laundry list of

things that you've already done.

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I think reframing, putting more

human into the job description

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would be really helpful.

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Karen Doak: Bringing up that point about

compensation models and comp teams and

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their role in it, can you just explain

that dynamic with a little more detail?

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Because I don't know how many

hiring managers are aware of, of

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how much of a role the comp team or

comp models play in that process.

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Jen: Yeah.

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I mean, compensation in most of

the organizations that I've worked

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in, they own the job descriptions.

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They create the job descriptions

because what they're trying to do

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within their compensation model is

make sure that they have levels and

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different, , requirements to allow for

a different comp level to be achieved.

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So you'll have certain years of

experience or certain education that's

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required to hit a comp level, and

then you go to the next level up, you

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have to have a job description that

warrants a larger compensation package.

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So your scope has to increase

or your, , re- responsibility

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of management has to increase.

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And so compensation is creating the

base of the job descriptions to make

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sure it fits into the leveling of

the jobs and the ladder of the jobs.

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And so then when the hiring manager

actually gets it, that they wanna add

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on all of the intricacies of what the

person's actually doing and to kind

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of tailor it, and that's when you

end up with these three-page long job

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descriptions that are really very hard

to understand what you actually need

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Karen Doak: Yeah, I've seen a lot of job

descriptions that, again, have gotten a

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lot longer and are starting to read like

wish list or definitions of a unicorn.

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Wondering, why you think that that

sort of, uh, process or dynamic keeps

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happening when we know it's not the most

effective way to hire and when we know

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it's eliminating so many strong candidates

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Jen: Well, I think that there's this,

fear of missing out, FOMO moment, that

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is happening for a hiring manager.

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A lot of hiring managers don't hire

that frequently, so when they have

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a position that is open, they think,

"Okay, this is my chance to get all of

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the skills and all of the competencies

that I want into this magical person."

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And it's a wish list.

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It becomes this very unattainable

wish list of things that they

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wanna achieve in one person.

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And unfortunately, they're not

taking into consideration, well,

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what does success actually look like?

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What does the person

need to have for success?

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A, that could be very different

than a wish list, and B, it

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could be much more minimal.

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Uh, to be successful, they need to have,

you know, three competencies, and their

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wish list is 15 requirements, right?

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So I think it's instead of thinking

about all the things I wish I could

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have on my team, and this is my only s-

chance, and I-- this is the only person

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I get to hire this quarter or this year.

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Instead say, "Okay, what does

success look like for this role,

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and how do I allow a, a variety of

candidates that have different lived

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experiences to bring that competency

or that skill to the forefront?"

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And opening their aperture of thinking

of what could success look like.

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Karen Doak: On the other side of it,

and something I've seen, especially

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in startups, especially where you, you

have an environment where a lot of roles

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are created based on necessity and, and

short-term and not necessarily long-term

158

planning, where the job gets fully

defined by the last person who held it.

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And instead

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Jen: Yeah

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Karen Doak: "I want another,

account manager," it becomes,

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"I want another Sarah," or you

know, "How do we clone Rachel?"

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Or whatever, to sort of define the role.

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and so I, I'm, I guess I'm

really wondering from an expert,

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is this a recognized pattern?

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Am I just describing bad

companies I've worked for?

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How often is this happening elsewhere?

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Jen: Oh, yeah.

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That's very, very common.

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And, and, you know, this is also something

that happens, um, in broader kind of

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HR, um, dynamics when people start

thinking about people versus roles.

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And that happens when you think

about, you know, a critical role.

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You start to say, "Oh, that's

Sarah," or, "That's Rachel."

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No, that's the person that

has become critical versus

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the role is actually critical.

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So when you think about succession

planning or, you know, you're trying

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to have a deeper bench in a certain

skill, you're, you're wrapped up in the

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people versus the actual role or skills.

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It's, it's just a common thing that

happens and especially when you

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have high performers, you wanna try

and replicate that high performer.

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You wanna try and say, "Okay, all of these

ki- skills and competencies that this

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person had, we wanna have that again."

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And what that does is it really

eliminates the creative thought

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process of looking at the team and then

looking at the demands of the market

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to figure out what does the team need

in the next 12 months or 18 months?

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What are the skills that are growing in

the space that we need to try and find?

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And then if it's not core skills, soft

skills and competencies on making the

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team stronger, then that's another

place where you may not need the

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exact replica of Sarah or Rachel.

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You really need to think about what

the dynamics of the team require,

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and that's another place that a

lot of hiring managers just don't

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pause and have intention for.

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And it, it goes back to

what you were saying in your

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chief of staff conversation.

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It's like this reaction and this

fast-moving pace prevents this

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intentional what are we trying to solve?

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What is the problem that this role is

trying to solve for, and how can we bring

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the right skills at this time to the role?

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Um, and, and that's something I

think every hi-hiring manager I've

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ever worked with suffers from.

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Karen Doak: So as part of that, it feels

like, you know, a key step that needs to

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happen is having a really neutral review

of the role and the job description,

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something that you mentioned to me.

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Um, does that require to

actually a truly neutral review?

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And, and why is it so hard to do when

you actually have this opportunity of

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having watched someone leave or fail

or not be as successful in the role,

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you actually have that perspective

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Jen: Yeah, I think the neutrality of it

can come in with multiple perspectives.

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I think that can add a lot of value.

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If you have a hiring manager and they

have the position open on their team,

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and they create the job description,

but they don't have anyone outside of

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their de- department or team look at

it, they don't have anyone else give

213

feedback, that I think is a, uh, an area

where they could, you know, improve.

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You could definitely say, like, "All

right, this is our common definition of

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a project manager level three," right?

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Project manager level

three, we know what that is.

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But then neutrally look at,

well, what does the team in this

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space and in this dynamic need?

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And that might mean someone a

little bit more senior giving

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some perspective, someone from

a different cross-collaboration

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giving some perspective, right?

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It, it could be an opportunity

for other inputs to come in other

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than just that one department.

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And I do think folks get a little

bit territorial when they're hiring

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because everyone's fighting for budget.

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And so if it's like, "Oh, I

got approval to hire, I'm just

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gonna keep it on my to-do list.

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I'm not gonna share it with anyone."

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And ultimately, no, they need to get

perspectives from other people and,

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and, and have that kind of combination

to go in to look to say, "What does

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the real success candidate look like?"

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Um, and then also I think there's an

opportunity to bring market data to

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those conversations that's often missed,

to be able to say, "Hey, when I look

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at other job descriptions out there,

there are these three things that

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are always listed, and we don't list

those things in our job descriptions.

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Is that on purpose?"

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And that can be a recruiter's

responsibility to bring that market

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data to the table to say, "Are we

focusing on a certain project manager

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that doesn't have these skills?

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Are we missing something, or

is that not, you know, a space

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that we wanna compete in?"

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And I do think that that kind of

competitive labor market intelligence

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is really-- it's kind of a, a best

practice, initiative for recruiters.

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Karen Doak: Having been a hiring

manager, you're absolutely right.

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Like, when you have that gap, and you have

that budget, and you have this opportunity

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to hire, it feels like this is my shot.

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I don't wanna start going into

Hamilton lyrics, but it's like

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this is my shot and my opportunity.

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And it, and I, I completely understand

that, that a lot of human nature

250

takes over, where you wanna take

that, uh, opportunity and make

251

the most of it to solve whatever

problem of the moment, uh, you

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Jen: Yeah.

253

Yeah.

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I mean,

255

Karen Doak: perspective helps

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Jen: this-- the human element is

something we just can't underestimate.

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I mean, I think the other part of this

is, like, you know, if a hiring manager

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has urgency, and they really wanna make

this a fast hire, they will prioritize.

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They will make this happen.

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They will attend every interview.

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They will review every resume.

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When they don't prioritize

it, the recruiter knows.

263

They don't show up for check-in meetings.

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They don't review resumes.

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They flake out on interviews, or

they delegate to someone else.

266

That hire is going to be set

up for less success than the

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very engaged hiring manager.

268

And, and I appreciate that they are tasked

with way too many things, and they're

269

pulled in all the different directions,

but when they prioritize that hire, what

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they're doing is really saying, "Okay,

I'm gonna invest so that this person is

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onboarded successfully and that I don't

lose a single stitch of time here."

272

Whereas if they get overwhelmed,

and other priorities take over,

273

it's, it's gonna be a harder fill.

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And generally, what happens is

the job is open for a long time,

275

you get inundated with candidates,

and then the hiring manager's

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like, "Well, I wanna see them all.

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I wanna see all 20,000 applicants."

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And you're like, "That's

impossible," right?

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And so it's a downward spiral.

280

If you, if you have a disengaged hiring

manager, you know that requisition's

281

gonna be open for a long time, and

it's probably gonna be something you

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have to start over at some point.

283

Um, you can kind of map this stuff

out when you've been around long

284

enough to know this is what's gonna

happen here, which is so t- terrible

285

to be able t- to say, like, "Look,

we don't have to go down this mess."

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Like, just follow our instructions

a little bit, be engaged at the

287

front end, and all of this will

be much easier down the line

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Karen Doak: Jen, my entire life

is me wishing that if more people

289

took my advice faster, we would, we

would be moving at a different rate.

290

, Actually the, the point of the process

and engagement in the process is

291

something I'd love to talk about.

292

I don't know what sort of process

adjustments you've seen or observed, but

293

these things that sort of get put in place

where no one is thinking about either

294

the candidate experience or just the

general, like, we need to keep this moving

295

.

Jen: Yeah, the interview process in general, it just is laden with

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bias and, uh, it's laden with, you

know, kind of old school practices.

297

Oh, we went to college together, we

were in the same fraternity, we were

298

at the same golf club, whatever it is.

299

And it just eliminates so much

opportunity for people that don't have

300

that recency or, or proximity, uh,

to the person that they're meeting.

301

And so I think if this, uh, this

age with AI, with all of the changes

302

in the candidate applying, right?

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The candidate can apply that

much faster to so many jobs.

304

There has to be a rethink of like, what

are we doing to assess this candidate, and

305

what's the experience that they're having?

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And the experience that

candidates have can make or break.

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First of all, the job

market's gonna swing back.

308

It always does.

309

And so while it's an employer

market right now, it will shift

310

back to be, a seeker market.

311

So I think just, um, adding a little

bit of humility into a job experience

312

or job-seeking experience would be

beneficial for most organizations.

313

Karen Doak: I, I actually, that point

about evaluation and bias is a big one,

314

and especially that the term culture

fit, which gets thrown around a lot

315

and is very hard for anyone to define.

316

And, and the secret definition tends

to be, I like this person, or I didn't

317

like this person, uh, or they reminded

me of this person I already know.

318

Jen: Yeah

319

Karen Doak: again, is what,

which is what perpetuates bias.

320

but does feel like we have all of these

other ways with technology to screen,

321

to reduce it, and yet at the same

time, because volume's high, someone's

322

college friend or frat brother is still

able to get to the front of the line.

323

And so I'm just wondering what

are realistic solves to make sure

324

that we're not allowing bias to

enter through the culture lens, um,

325

everything that is happening right now?

326

Jen: Yeah, I, I, I think this culture

add space or culture fit space, I'd love

327

to see repurposed to culture add, right?

328

And so like being able to say, "We clearly

understand what our culture is," which

329

I don't think a lot of companies do.

330

I think that they think they do,

but they don't actually hold a

331

mirror up to themselves and say,

"Here's what works in our culture.

332

We're very transparent.

333

We're brutally honest.

334

Uh, we over-communicate.

335

We have very flat lines."

336

Whatever it is, right?

337

To be able to say in a, in a handful

of sentences, this is what makes our

338

culture and this is what works well.

339

People succeed in this culture.

340

Startups, they generally have their

own culture, which is startup culture.

341

You have to be flexible, you

have to pivot, you have to

342

be able to do lots of things.

343

You have to be, you

know, sense of urgency.

344

Okay, so then to be able to say,

um, what could we add to the

345

culture that would make it better?

346

What, what traits could we add instead

of having the exact same thing over and

347

over again that would make us even better,

which would accelerate our culture?

348

Nobody wants to work with a jerk.

349

But the reality is if success means,

hey, we have to communicate every day

350

and communication is key, then that's

a real thing to evaluate around.

351

But if it's actually we don't have

to communicate, the product is

352

what the product is, and if that

person can deliver the product and

353

we're not communicating every day,

success can still be made, right?

354

And so I think it's evaluating what

does success look like and then

355

how does that add to your culture?

356

Karen Doak: I love the reframe

of culture fit to culture add.

357

I think that's just such a great way

to, to phrase it and think about it.

358

And I, I think some of the most successful

hires I've made have been little

359

unconventional or brought something new.

360

Jen: Yeah, I do think thinking just

broadly about the profiles of the

361

people that you're bringing in and

thinking, "Well, they've never done

362

X," and shifting it to, "Well, they've

done all of these other things.

363

How are all of these other experiences

and skills coming, and b- what

364

is that bringing to the table?"

365

Instead of, "They're missing something."

366

And I think it's like the abundance model

versus the scarcity model, and when we

367

get into a hiring situation, we kind of--

our defenses take us into a scarcity model

368

versus saying, "No, there's more out here.

369

There's more experience.

370

There's more perspectives.

371

Let's think abundantly."

372

And then that shifts the model of

the way that they consider people,

373

Karen Doak: If you could get a hiring

manager to answer three questions, to

374

like clearly define a few things before

a role gets posted, what are the sort

375

of priority things you would want to

make sure they're crystal clear on?

376

Jen: Um, I think one of the things you

wanna get a hiring manager to think about

377

is, is this position, um, creating output

or creating a, a growth trajectory, right?

378

Because if the, if the position

is very stable and it is an output

379

type of position, sometimes that

can create parameters that you

380

just-- you have to work within.

381

But if it's a growth or a really

trajectory, kind of high trajectory

382

position, then you really want the

person to be able to describe what does

383

success look like today, and what does

success look like in twelve months.

384

So I think establishing that

one parameter first is, is key.

385

And then I think it's looking at the

dynamics of the rest of the team to

386

be able to say, "Okay, hiring manager,

you have four or five direct reports.

387

Can you talk about the gaps that

exist on your leadership team that

388

this person could potentially fill?

389

What are the competencies as a

team that you wanna be able to

390

double down on or expand on?

391

And could that person-- could this role

bring those skills and competencies?"

392

So one is, is it a stable position

or is it a growth position?

393

Two, how does the position

fit in with the broader team?

394

And then three, what is

their urgency on filling it?

395

And oftentimes, a hiring manager

wants to sit on a job for a variety

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of reasons, but they may not be

able to, like, mention them, right?

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It might be kind of hush-hush, "Oh,

I want this person to be able to

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move from a different department, so

I'm not gonna advertise externally."

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Like, there's always some

politicking that's happening.

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And so m-- just asking them, like,

"Is this something that you really

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wanna fill quickly externally?"

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And if you can gain a bit of trust

with them and they can give you

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that answer honestly, you will save

yourself and candidates so much time.

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Karen Doak: That's awesome.

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And I guess just with your past

experience and with where you're seeing

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the market today, you know, do you

feel like this is going to get better?

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Do you feel like there's a version of

this where we're just staying in the

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same dysfunctional state on repeat?

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How do we collectively be the

change we wanna see in the world?

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Jen: Well, it's interesting because

I feel like this is the place that

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startups, uh, can really take charge and

do things differently because they can.

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They, they have that flexibility.

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Um, and someone was telling me, you

know, that they're doing more pop-ups

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at a bar or pop-ups at, you know, a

hackathon, and they're giving job offers

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after the hackathon because they can

actually see the people in action, right?

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Like, I think where there's real ingenuity

of saying, "Hey, we have an opportunity.

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We can hire 10 program-programmers

for whatever the task is.

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Let's set up an activity where they

come, and they perform, and then

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we give them offers right then."

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Candidates would love that experience.

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Hiring managers would get more choice

and be able to see them in real time.

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I think when there's scrappier startups

that can do things differently and

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just completely break the mold, I think

that's where you have real opportunity.

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I think the bigger companies, um,

they're gonna be stuck in, in this for

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a w- a long time because hiring has

not really evolved in decades, right?

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It is basically the same process

that our parents had, um, although

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it's a little bit more automated.

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But, like, the whole interview and

feedback, like, the basics of the hiring

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process has been the same for decades.

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And so the way to really change it, I

think, is for smaller companies to be able

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to say, "We're just not gonna follow that.

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We're just not gonna do

those things anymore.

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We're gonna try it completely different."

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Karen Doak: Well, Jen, thank

you so much for your time today.

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I really appreciate it and, and all

of the insights you were able to share

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Jen: Yeah.

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Thank you, Karen.

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And for anyone listening, I'm really

excited on working with leaders on

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their recruiting process, but also

just talent management in general.

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Um, it's been my passion to be able to

help, uh, small companies, mid-sized

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companies think about how talent

evolution can really expand their growth.

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And so my biggest question to leaders is,

you definitely have a business strategy,

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but do you have a people strategy

that is gonna help you execute that?

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So, thanks.

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Karen Doak: Wonderful, and I will make

sure that your contact information

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is in the show notes so that anyone

who wants to follow up with you can.

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Jen: Awesome

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Karen Doak: a few things I wanna

leave you with from this conversation.

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First, the job description

is not a formality.

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It is the very first document in the

hiring process, and if it's wrong, if

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it's a wish list, if it's last year's

description with three new bullet

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points, , if it was written by comp

for salary banding and never touched

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by the person who actually needs to

fill the role, everything downstream

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is then built on a bad foundation.

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The interview process, the candidate

pool, the offer, all of it.

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You cannot hire your way to

clarity you didn't have on day one.

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The second thing, Jen made the

point that every open position is an

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opportunity, not just to backfill, but

to actually look at what the team needs

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now in this season, in this market.

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That requires intention, and it requires

someone to stop and ask, "What does

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success actually look like in 12 months?"

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Not, you know, what

did the last person do?

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Most organizations skip that

step entirely, and the ones that

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don't are the ones Jen described

as actually getting this right.

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And the last thing, and this is the

one I'll be thinking about for a

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while, but culture fit is doing a lot

of harm dressed up as a compliment.

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Culture add is definitely the right

way to be thinking about things.

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Not who feels familiar, but what does this

team need that it doesn't already have?

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What perspective, what skill, what

lived experience would make us stronger?

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This is a fundamentally

different hire than cloning the

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last good person in the seat.

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So if you're in the middle of a search

right now or about to kick one off,

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I'd start there and really think

about , those key questions that

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Jen gave all of us to think about.

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I'm so grateful for her insights today.

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And I'm Karen Doak.

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This is Okay, Actually, where

we get clear, get sorted,

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get going, and stay sane.