johnpfeiffer

Behind the scenes of the challenges for a Hiring Manager

Hiring is more than just a single decision

A lot of interviewing advice is for candidates. I wanted to pull back the curtain on some experiences and tips for hiring managers, especially if it's your first time and you just got a headcount. =)

(Hopefully this is also useful if you're training people managers or ICs on the whole process)

Hiring exists to solve a business need. It can take as little as a few weeks, as long as a year or more. Like many management responsibilities, it is more than just a single decision, often it's creating an effective system.

The Hiring Manager is always accountable for the decision to hire, the process of hiring, and the results of hiring (or not hiring)

Backstory on How a Role Opens Up

There is a lot more to the story for a straightforward job posting like "Senior Engineer".

Here's a short list of reasons that a position may have opened up - and how that influences the hiring process:

  • rapid growth of users/customers
  • gaps (think reliability, bugs) due to growth
  • very lean team reaching a breaking point
  • someone left
  • someone was asked to leave
  • a completely new team (or even whole new initiative)
  • org shuffle
  • newly discovered gap in critical skills

Growth headcount is a calculated bet: the organization is investing in a direction.

The approval can hinge on this being aligned with larger leadership strategy and initiatives, and who specifically has budget. Opportunity cost can be subjective, and if this hire comes at the expense of another team?

People in the existing team may wonder why someone's getting hired "above them", or if it means more work and distraction doing interviewing and onboarding, or even worry about this being the beginning of them being replaced.

Backfills are the most straightforward: the organization was paying for a certain amount of work to be done and now needs a replacement. While the approval can be straightforward due to previously allocated budget, it can also mean there's prior expectations.

The existing team/colleagues may be concerned: either that the new person won't be able to do as much as their previous colleague, or that they'll have similar or worse flaws as their departed coworker.

The old saying is "Fool me once, shame on you, fool me twice, shame on the Hiring Manager"

Either way, the team is carrying extra load until the new person starts.

Shuffles and Discoveries are the most at risk. Sometimes the org or plan changed, and it could change again. These headcount may not map cleanly to a business narrative or stable org structure. Sometimes the approval was verbal and never really hardened into a durable commitment. Maybe leadership wants a new capability, but the business case is still fuzzy.

People may ask why someone new is needed for a specific new skill or background/experience instead of uplevelling existing folks.

Ultimately it will be asked:

If this role exists, what other role does not?

Deciding the Level

Here's where the challenge gets harder. Level determines compensation band, which determines budget.

Does your budget really support current market rates for that senior engineer you're sure you need?

What's the distribution of seniority in your team(s), and even the wider org?

Are people needing a mentor - or mentees?

There can be pressure to down-level (which creates room for others in the team to step up) or up-level (which adds skills and bandwidth that may accelerate/improve the team).

Then there's reality of who's applying: if you post for Principal Engineer it's a smaller pool of candidates - which can make finding the right one take a lot longer (or cost more).

Also, candidates at higher levels (more scope, more comp) need to go through more vetting. That may mean navigating cross-org or "all-the-way-to-the-top" approvals.

And candidates may shy away from the increased requirements and extended process. You may have to innovate new ways of assessing these rare candidates, and get approval for that new process too.

One critical tip: if after a couple of months the candidate pipeline isn't quite matching - revisit the job requirements and level.

Something I've personally seen: opening a role at Senior for a wider pool, then having an amazing candidate who will only accept Staff, needing to go back to HR/Finance and renegotiate. In the extra time it took to renegotiate the level, the candidate accepted another offer.

Tools of the Trade

Politics: the art of influencing others.

So first get the facts and strive for first-principles thinking:

  • What does the company truly need now and for the next 12 months?
    • Get feedback from your manager, your manager's manager, and your peers
  • What element needs to be added into the chemistry of the team?
  • What can you truly afford - now and during the next compensation and promotion cycle?
  • What's the opportunity cost for every month the role isn't filled?

Avoid hiring for vanity metrics ("doubled my team") or empire-building ("never dependent on other teams").

The uncomfortable truth: sometimes headcount is assigned because of existing relationships or to keep someone happy.

Long term credibility comes from being seen as objective with decisions that lead to achieving the larger goals, from having a well documented track record of delivering results.

Helping new managers with their hiring process has been some of the most rewarding and impactful work I've done as a people manager:

  1. I helped a peer advocate for and successfully hire 2 great candidates when there was only 1 headcount available by looking at the company's own 12-month forecast
  2. I've pointed out some missing topics in interviewing loops which raised the quality of the candidate debriefs
  3. I've supported a Manager who struggled to say No to everyone on her team, when they kept saying "Yes" to every candidate; via private 1:1s everyone came to understand the real impact of a bad hire
  4. I've even transferred people to another team when they really needed it but didn't have headcount

Writing the Job Requisition

The job description you see on a careers page has been through a journey to get there. It's actually a myriad of compromises about what the manager wants, the team needs, what the company can support and how the company presents itself externally.

It starts with a hiring manager writing briefly what they actually need. This is the important part: documenting what would truly move the organization forward, not just a wish list.

Then the manager of the hiring manager looks it over and considers the context of org priorities and patterns, historical trends for similar roles.

HR reviews and adjusts it for legal/company policy adherence.

Then recruiting edits it for marketing/SEO, company messaging, and consistency with existing job templates.

Since the final polished posting can be different from the original Hiring Manager's version, experienced candidates know to ask, "What does success look like for this role in the first 6 months?"

This is smart because it begins the conversation of alignment on impact - everything on the "required" list may not be needed until month 9+

Working Together with your Recruiter

Maybe you've been wondering the whole time: wait, the Recruiter's last?

If they are last and they just take the req and blindly post it then you may have a long and painful process of starting with poorly-matched candidates =(

The recruiter is not your assistant, they are a skilled professional in a specific domain to achieve company goals.

The collaboration between hiring manager and recruiter is essential for success. Recruiting/Talent have Key Performance Indicators about the number of resumes and candidates screened, interview funnel conversion rates, offers vs accepted, and candidate engagement feedback.

They are also almost always juggling multiple reqs and pipelines at once.

A good recruiter asks questions like:

  • For candidates, what's the narrative on why this role is open, why the team and project is great?
  • What's your dealbreaker(s) for passing on a candidate?
  • What's one requirement or skill you might compromise on?
  • What are examples of existing employees that'd match the role?
  • How diverse is your team, and how diverse is the interview panel?
  • How long would you wait before down-levelling to widen the candidate pool?
  • How willing are you to up-level or consider a signing bonus for a great candidate?
  • How will the candidate perform and feel after 6 hours of back to back interviews?

They will tell you historically how long it usually takes to hire this role, if it's a "employer's market" or "candidate's market", and bluntly: that you might be looking for a flying unicorn.

Calibration and Sourcing

Early alignment at the top of the funnel saves a lot of time and effort: what profile is most similar to candidates who will do well during interviewing and get an offer.

An exercise I've been through many times to great effect is having the Recruiter provide a list of randomly selected candidate profiles/resumes and scoring them to 1-5 for how "strong" they seem for the role.

While the first round can be async, what's truly important is to have an actual meeting talking through the Why one candidate really seems better.

Sourcing is finding the channels and methods to reach out to candidates. Your Recruiter/Talent team may know the currently best performing places. Managers and ICs may know the industry niche or geography-specific places that are really high signal.

Finding those proxies for "Who will probably do well" and "Where can I reach them" are the foundation for your pipeline.

  • Referrals: traditionally the strongest positive signal as someone actually worked with and vouches for this person. These candidates will understandably get special treatment, and it requires diplomacy if things don't work out.
  • Sourced: they didn't actively come to you, they were found because they fit your target profile. A personal message from a Hiring Manager starts a human connection.
  • Organic Inbound: high volume and low signal - anyone can click to apply. So time consuming it often needs automation to filter and prioritize, sometimes it even needs (time delayed) auto-rejection emails.

Setting Up the Interview Loop

Candidates, and even Interviewers, rarely see all the machinery underpinning the Interview Loop.

There's usually an existing framework or template in the company, but as a Hiring Manager you may need or want to adapt it.

How many interviews, what type, and in what order:

  • Recruiter Screen: cross check their resume with reality, quick company/culture fit, scratch test on a few topics
  • Hiring Manager Screen: is this worth everybody's time?
  • hands-on technical: core responsibility of the role
  • architecture: systems design and big picture thinking
  • cross-functional: input from adjacent disciplines like Product or Quality
  • presentation: previous project or case study
  • simulation: a scenario that ramps up
  • behavioral: experience, judgment, career ambitions
  • executive: department/company culture fit, adaptability, future promotion potential

Will you have discrete phases and gates where candidates get evaluated like Recruiter/Manager screen, Tech Screen, Onsite? Or a more continuous sequence of sessions?

Since there's an additional cost to your org for every additional session you add, consider the heuristic of increasing investment as you gain confidence and need deeper signal.

And if the candidate fails on a critical area, do you continue with the rest of the sessions?

Choosing interviewers is like casting for a show: you need an experienced expert for each topic, and you need their backups for availability.

I've found being specific on your priority order and max number of interviews one employee should do per a week is critical to keeping things smooth and sustainable.

You may also have to borrow folks from a peer's reporting chain which is a delicate conversation about priorities and "for the good of everyone by increasing the company's overall capacity".

Training Interviewers

Training interviewers before they actually interview an external candidate is incredibly important but always ends up so low a priority that it defaults to "learning on the job" - to the detriment of everyone involved.

Bad outcomes can range from "missed a good candidate" to "waste of time" to "lawsuit against your organization".

The Hiring Manager should write out the minimum acceptable signal for each part of the loop. What's being used to identify good vs weak?

Get clarity on what cannot be legally asked in an interview, and on when and how to discreetly end an interview if it goes off the rails.

Then meet with prospective Interviewers, as a group or individually. Talk through the job req, their specific topic, time management and the expected usage of time (i.e. 5 mins intro, 35 mins on topic, 5 mins candidate questions).

During this process you can and should get feedback from your experienced people about the role's requirements, what should be asked, and what really matters in terms of concrete signal.

For those less experienced overall, or on a specific topic, some useful techniques are mock interviews (you play the role of a candidate) and shadowing (quietly observe in the room) an experienced interviewer's session.

Structured Interviews

Structured interviews (especially for subjective areas) improve the objectivity and effectiveness:

Scheduling Challenges

Scheduling can be a large invisible hole in the hiring pipeline.

It's hard enough to juggle your team's existing responsibilities while prioritizing the candidate's availability, but you may also have to coordinate calendars for cross-functional peers or a whole panel session.

Stuff happens: someone's sick, there's a production or security incident, the candidate last-minute cancels and needs to reschedule.

You'll need debrief meetings too - ideally the first ones are synchronous so you can improve on shared understanding of calibration: what was a good score, a strong candidate, and why? Any yellow or red flags and best questions that uncover those?

If you're lucky there's a dedicated scheduling coordinator, fancy software that matches availability, or your recruiter is a saint and a calendar savant. You should be prepared to be involved: as hiring manager, you know your team’s calendars, constraints, and priorities better than anyone else.

Hiring Manager Interviews

This is a unique piece in the puzzle because no one else can really own:

  • Can I adequately support their professional needs and career ambitions?
  • Will I be able to manage them? Would they listen to me and take feedback, will we get along professionally?
  • What might I need to adapt or prepare the team for during interviewing?
  • Do they add something special we just don't have, that I didn't even think to ask/require?
  • Will this person thrive here?

Delegation at its finest: depending on your team and peers to evaluate role specific skills, communication, planning, etc.

This is your opportunity to ask open-ended questions with follow-ups. Get them to open up so you can understand motivation, self-awareness, judgment, and professional style. How do they handle stress and accountability?

The classic question is:

Tell me about a conflict with a peer or your manager, and how it was resolved?

One of my personal favorites:

Where do you see yourself in 2 years time, even regardless of this role?

Tech Screens and the Onsite

There is already a lot of good material on designing technical interviews, so I will not try to recreate all of it here.

Here are a couple that I like:

Debriefs - Data and Humans

Be clear with yourself and everyone on the debrief panel:

This is an attempt at deciding fit of a candidate for a role and organization at a given moment. It is not a personal or professional judgement on the individual

Everyone is "in a room" to work towards a decision. It's not a debate, it's a fact finding mission. How much signal can you extract from the process?

Scorecards appear clinical and objective, but there are many known cognitive biases to watch out for:

  • anchoring or recency bias (first or most recently seen as the best candidate)
  • similarity bias (selecting for perceived similarity to the interviewer: background, interests, communication style, etc.)
  • liking bias (charm is not the only criteria)
  • prestige bias (brand or fame instead of focusing on evidence)
  • stereotyping
  • attribution error (no skill or just nervous?)
  • groupthink

Interviewer feedback quality will vary, some people write detailed, structured scorecards with specific examples. Others write "Yes, hire".

Some of your interviewers will have a really high bar, while others generally default to yes.

Your role as Hiring Manager is to improve the process: set expectations and get the data.

Having a concrete scoring rubric with examples converts some of the subjectivity into objective numbers. Enumerate ways for candidates to score points, and even consider transparently sharing your scoring rubric with the candidate.

The longer it takes for you and your interviewers to understand what "good enough" looks like, the more likely you are to lose that window of opportunity for an amazing fit candidate.

I've found it goes most smoothly if there's a clear Facilitator and each person provides their feedback with an opportunity for questions. Not a place for the "loudest voice wins", or detours into technology preferences and ideology.

It can feel like the hardest part to sit on your hands and keep your mouth shut, but you really have to listen and stay curious

*I have found that sometimes you can't or shouldn't cleanly tell the interview panel whether you're making an offer - you may need further discussion with your manager and may not even yourself know *

The Decision

The hiring manager makes the decision, informed by the panel. You may want unanimity. You need data. You will deal with the consequences if you hire against consensus or over objections.

If you pass on someone, then maybe you'll see this person again when they're the Interviewer and you're looking for a job.

One of the most memorable debriefs I ever experienced was a group all giving a barely-good-enough score "Yes to hire". Then when I asked each person "Would you sit next to this person and work with them for the next month", an instant "No".

Always Be Closing

Every touch from the recruiting team and interviewer is a signal about your organization. Great candidates have options and other offers.

While the recruiter handles logistics and total compensation offer, you should "close" personally, because after the dust settles this person will become your direct report.

Call the candidate on the phone and tell them why you want them specifically. If it's appropriate, take them out to coffee or lunch, and sell them on the broader vision of the team, the work, and their growth.

The goal isn't perfection or winning, it's to have a strong foundation and keep improving.

The Offer and Everything That Can Go Wrong

Now that you found someone you want to hire, you can find out where things stall, fall apart, or get weird.

The Total Compensation Package is usually a combination of salary and equity, hopefully part of a pre-defined compensation framework that maps to existing employee levels and salary bands.

https://blog.john-pfeiffer.com/compensation-planning-is-sudoku-with-feelings/

Usually a number of people will need to sign off on the Offer:

  • Your manager (and maybe even someone above them): is this really what the org needs right now?
  • HR: any discrepancies or irregularities in the interview process, background check, employment conditions, etc?
  • Finance: this will become an ongoing expense to the business - was it really attributed/budgeted correctly?
  • Maybe even the Founder or CEO

In a chaotic or high friction system this can cause delays - long enough to frustrate or lose a candidate.

"Ghosting" or never getting back to a candidate, at any stage - especially this stage, is a reputational black eye

Comp negotiation: The candidate wants $X + 20% - is that really doable? In salary band range? How does it look compared to existing team members and employees?

The recruiter (and/or an internal referrer) may be advocating for the candidate.

Are you willing to push your Manager/HR/Finance for this?

Sometimes the first offer feels like a deliberate fiction: of course there's 5% wiggle room, counter-offer back.

Similarly, be careful to not negatively judge a candidate who negotiates: hate the game not the player. Understand they have their own needs and goals - this is one of the few places where someone has leverage with their (prospective) employer.

Sometimes candidates take a long time to consider the offer. Maybe working through a competing interview loop or waiting for a counter-offer or going through a life event. Lean into your Recruiter's people skills to diplomatically reach out. And keep your process going

Counteroffers complicate things. The candidate's current employer, or a competing employer have offered them something "better".

Take a pause before you act. You might not need to counter, nor resign yourself to losing the candidate.

If possible discover what's compelling about the alternative: title? autonomy? equity? "More cash" can mean immediate increase or a future promise, or a larger (future) bonus.

Make your case persuasively, but don't oversell or overpromise. I've hired someone at top of band and then really struggled 10 months later when they wanted a substantial raise but they didn't meet the bar for promotion.

Continuous Improvement

Hiring is always a moving target: needs of the company or team change, candidates appear and disappear from the market.

Having written artifacts for each part of your system means you have a transparent reference for everyone, and a place to update and roll out improvements.

After a few weeks (and a lot of resumes) you should already be learning from the funnel: analyze which things aren't working?

As you experiment with changes monitor using your (ATS aka applicant tracking system) dashboards.

On a single req I've actually experienced changing almost every part from requirements to job posting title to role title and level.

When things aren't working, start from a charitable perspective and use the "blameless post-mortem" and "5 Whys" techniques.

This can feel like a lot of pressure and a big decision. A bad hire impacts the team and maybe even many others in your organization, which is why so often "no hire" is the safe choice.

Also though, economic or political winds may change and your job opening will be closed unfilled. It's a measure of your resilience to learn as much as you can from the experience and improve for next time.

Hiring can be emotionally exhausting. Know that you too will "level up" and get better by doing it.

I definitely remember the naive time I closed a req after a candidate accepted our offer, and then the day they were going to start we learned they actually decided to go with another company

Measuring Success

Of course 100% accepted offers sounds great, unless it's a sample size of 1. Or new hires don't reach the 90 day mark. And having more headcount is also more headache at annual review and compensation planning.

Consider some other ways to measure:

  • candidate experience becomes marketing for your organization's reputation as an employer
  • interviewers will remember if things were well organized or chaotic
  • a well documented system elevates the process for everyone

Great management isn't just intuition and a few good decisions. Instead, like a "sports dynasty" or a finely engineered software system, it reproducibly generates great outcomes.

Hiring is part of the long lifecycle of your relationship with someone, from candidate to direct report to transferred to another team to "alumni".

Resources

After you hire then it's time for onboarding which is a whole different blog post. =]

Here are some other good resources on Hiring:

Bonus Update - How to update an Interview Loop for AI

I led an update to our engineering interview loop once it was clear that engineers were effectively using AI every day to do the work.

During interviews we were already getting awkward signals: candidates quietly using LLMs during coding screens, long pauses, eyes off-camera, and trouble explaining their own code.

I split the loop into two parts: a non-AI fundamentals exercise first, then an AI-required round where candidates show how they actually work with prompting, evaluating generated code, adding guardrails/tests, debugging, and refactoring.

That made the process far better: transparency removed the awkwardness, candidates relaxed, and some blew us away. The artifacts made debriefs much stronger too: we could evaluate judgment and approach, not just "code".

With agents, the next hard question is what “bring your dev environment” should mean in an interview?

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