How to Hire a Head of Talent
Just once in my talent career I’d like to go through an interview process that didn’t feel like it was designed by 3 squirrels in Patagonia vests.
As a Head of Talent for startups - I’m interviewing with teams that need someone to come in and design interviewing - so we’re all in a painful chicken meets egg meets startup squirrel brain scenario. When I share my own interview experiences, friends gasp, colleagues' mouths drop open, I get long texts back in all caps. And those outside of talent go - “so you’re definitely not going to consider another interview, right?” And then I shrug and calmly explain that every interview cycle I go through is going to be terrible because I’m being hired to make it not terrible.
But this week I thought - I’ve never had to hire someone for my job - sure I’ve hired someone above me in my reporting line, below, you name it and I’ve recruited or supported a search for it. I’ve mentored and developed people into the job - but never sat down and hired…me.
So, here’s how to hire a Head of Talent for your startup.
First, treat this as an executive search. Stop clutching your pearls. This is an executive role expected to interface with every leader internally, represent and drive your brand externally, and build your company.
Ok, how do I do an executive search? Remember, I don’t have a Head of Talent.
Executive searches have 3 key ingredients:
Tight alignment on the role scope and what you need from your candidate today and 1-3 years from now (align amongst the: hiring manager, founders, interviewers, any existing talent team)
Overcommunication - you’re checking in with all of your active candidates at minimum twice a week, each time you speak with them there’s a commitment on the next outreach and touch point
Candidate driven conversations - expect to dedicate a % of your interview experience for the candidate to have a mix of informational interviews, selling conversations, product demonstrations, etc.
Build a Candidate Profile & Role Scope
Before you post the job or solicit your investors for referrals ensure you have strong alignment starting with the reporting line and responsibility scope. Depending on the size and projected growth of your organization this role may report into the COO, founders, or if you’re really ahead of the curve, your Chief People Officer.
Tip: The reporting line will signal to potential candidates their level of influence in the organization - which can get complicated if it’s reporting into a COO that also (for example) manages the revenue organization which pits your talent resources against the CTO’s hiring needs who does not oversee the talent team.
Responsibility and scope are critical - for candidates who have scaled out multiple organizations you’ll need to provide a path to or flexibility with titling and promotions. Today they need to get a talent team up and running, tomorrow they may help kickstart and oversee portions of onboarding or talent management. Being clear and upfront with where the role can evolve and where it will not will help differentiate your opportunity against others in the market.
Now for your profile! Your planned growth will drive a lot of these decisions - how many people do you need to hire in the next year (this is now your baseline for speed and scale candidates have achieved), what types of skill sets or industry specific backgrounds are you hiring for (this narrows your profile for types of organizations candidates have been in/around), physically where are you hiring (domestic, international), and finally where are you scaling to (e.g. we are 100 people today, 300 people next year, and 1,000 people in 5 years).
Now - look back at yourself (it’s reflection time). You’ve got 100 employees, some values on your website, a couple missives about how you’re building a unique culture, and the 401k plan is finally set up correctly. You need to hire 200 more people and some recruiters and and and…now ask yourself is that candidate coming from a 150,000+ person organization where they’ve been running a 60 person team and a $15M budget? Probably not. You need speed, quality, and efficiency when you’re building. Most importantly you need a candidate that has already gone through milestones you’ve yet to achieve. (And if you have a $15M talent team budget, call me).
Write a Job Description
Post self reflection - let’s write a job description. And I’ll be honest, every Head of Talent post I’ve seen has been half copied from the same 3 other posts out there. Write something original (ChatGPT doesn’t count) and it might look a little something like…
Our company does XYZ.
I know your marketing team built a beautiful 2 paragraph very fluffy and detailed overview of how you’re changing the world, but we need to know what this is so say it - are you a Saas company? Services? Do you build robots?
Why do you exist, what market do you serve, and what’s the market opportunity/cap.
We have money and understand it isn’t infinite.
Are you profitable? Nearing profitability?
Who are your investors?
How and Why are you growing (coming out of stealth, ready to add heads post funding, etc.)?
Here’s your boss’s title, why Talent is important here, and your scope. And how much we’ll pay you year 1.
Why talent is important to us is often completely left out of posts, interviews, and stumps half the leaders I’ve spoken to - articulate what kind of leader you want to drive this function (hint: it’s the person that will drive all revenue growth for your organization)
Scope definitely includes: hiring to headcount plans, talent operations, analytics, hiring/firing/developing a team, collaborating with leadership across the organization, vendor management, tech stack, and branding
Scope may also include: talent management, onboarding, supporting the people function as it stands up, domestic or international expansion elements, training, university hiring or early talent, DEI programs, and more
We have these top talent priorities.
Call out your top 3 recruiting pain points or goals that this person must focus on (can be time bound or milestones like: overall growth, hiring a new engineering team, etc.)
Our desired candidate has X skills and experiences, with these Y non-negotiables.
Tip: The more specific you are in your non-negotiables, the more committed you must be to that skillset being the “make it or break it” factor in your hire.
This is where you pull from your profile notes - do you need someone who has built out call centers in Texas? India?
Do you need someone who has scaled Series A companies up to 200 people? Or someone who can scale you to 2,000 people?
Do they need to know the nuances of hiring nurses, mechanical engineers, or factory workers?
(Don’t forget to say where the person will be - remote, onsite, hybrid, office locations)
Head of anything roles are tough to write because these leaders must have the cumulative experience of everyone in the function + the ability to be a strategic leader which lends most companies to publish long laundry lists versus compelling job posts.
Make a Plan
Phew, ok we have a profile and a job post, now what?
Now build an interview plan. That doesn’t suck. And close the conference room windows before the squirrels get in here and muck everything up.
An easy framework to begin drafting an interview plan for any role - break down each of your desired candidate qualifications into three buckets using your job post and any internal wishlist items across:
Technical Skills & Experience
Leadership Qualities
Company Values Alignment
Let’s use this interview plan:
Introductory Screening Call
Leadership Interview
Hiring Leader #1
Hiring Leader #2
Values Interview
Informational Interviews
Executive Close
Introductory Screening Call
Pick your top 3 requirements across everything you want in a candidate - those are going to be validated in your first interview, along with their desired next role, compensation, location, and all the logistics.
Sell: your company and the opportunity. Get detailed on resources, growth targets, the product, development and growth paths - beyond what you have on the website or job post. The candidate should leave this first conversation excited about your prospects in the market and the challenges they’ll get to tackle in the role. (Tip: make this the second half of your call so you can highlight selling points based on what the candidate shares in the first half).
Leadership Interview
Next, the candidate should meet with their future manager and dive into the “leadership” bucket with topics around: how they build and manage teams, recognition, performance management, how they influence others, build consensus around initiatives, and handle hiring managers at each level of the organization. In short - how do they show up as a leader, and how do they work with other leaders.
Sell: how they’ll be supported (and by whom), what the leadership culture is like within the organization, development and role scope opportunities.
Hiring Leaders (Technical Skills & Experience)
Now grab two of your most important hiring leaders (typically the equivalent of your head of revenue and head of engineering) and have them map out 1-2 of their biggest hiring pains that are unique to their organizations - either in maturity or skillsets. I.e. they shouldn’t walk in, pound the table and say they can’t get enough engineers. There’s nuance…so detail out that nuance. Those nuances and hiring pains should match most of items in your “technical” skillset bucket.
Each leader should have behavioral interview questions mapped out around the pain point, think: “We are struggling to differentiate ourselves in a market where there’s high demand for machine learning engineers and we’re just one of many companies trying to attract them. Can you tell me about a time when you faced a similar challenge and what were some of the solutions and results you were able to achieve?”
Sell: the candidate on your working style as a leader. Tell them what you’re curious to learn more about working with them, what you’d like out of a partnership, and what excites you about the challenges that lay ahead. You need a Talent leader that will collaborate with you, and they need to know you’re a hiring manager who will do the same.
Company Values Interview
Finally, your Values. For a Head of Talent, this is such a great opportunity to bring in someone like your CFO or Head of Finance or even your Marketing or Communications leader in. For your CFO, crafting an interview around planning processes, working style, and aligning it within your company’s values makes for an informative conversation (the candidate can learn more about headcount management, and the interviewer learns more about how they work with someone outside of the hiring process relationship).
I also love getting to meet someone in Marketing to talk about branding and how they want to represent the company to attract talent - which can be woven into your values through behavioral questions and open dialogue.
You’ll want to leave the Values conversation confident that your candidate’s behavior aligns with what you expect from your employees - and with either of these interviewers you’ll get to see an example of collaboration where the candidate is not necessarily in the “primary” position (e.g. the candidate will “own” the hiring process but not the annual planning process or the corporate brand identity).
Sell: partnerships and support outside of gaining favor with the CRO or CTO - the relationships in other functions like finance or marketing will enable Head of Talent candidates to be successful in thorny initiatives like a website rebrand or getting headcount plans.
Informational Interviews
Candidates need the opportunity to request and drive their own conversations which can and should happen in parallel to the process above - make this clear in your first screening call, and even provide a menu, which might include:
Product Demonstration
Recruiting team member(s)
People Operations
CEO meet and greet
Interim Talent Leaders or Consultants
Any members of the executive team not scheduled for the interview panel
Executive Close
Finally - you’ll want to end with a closing call - typically with your hiring manager, you’ll recap all of the positives, excitement, and address any of the candidate’s remaining questions or concerns. End this call on a high note and let them know when they can expect an offer!
Candidate Experience
Back to over communicating - you’ll want to pick one person to be the search leader - depending on structure this may not be a current recruiter or even the hiring manager. I’ve seen executive assistants, Chief of Staff, coordinators, and more in this role but ONE person must be in charge of communicating next steps, checking in, calling or texting the candidate to gauge temperature, and keeping your company top of mind for them. They should feel like the candidate’s advocate and concierge at the same time.
Declining Candidates
As you go through interviews you’ll find yourself refining your profile and must vs. nice to haves - so you’ll end up declining a number of folks along the way. General rule - if they’ve passed through the first interview - always offer a phone call to provide feedback. Feedback on why they’ve been rejected should be more specific than “other candidates were stronger”. For example: “We have other candidates with deeper experience in scaling out engineering operations in India which is one of our top 3 priorities this year.” Always say thank you, and offer to connect them to other startups in your network.
But I want them to show their work! What about a take home assignment?
Case studies or presentations are a great way to qualify a candidate’s ability to draft documents or build slide decks. They can provide an opportunity to present their way of thinking or approach to solving a problem. If drafting these materials is a critical part of the job, go for it, but keep this in mind:
Never ask a candidate to do free work. Do not give them a problem you are currently trying to solve, or a prompt that would result in work that could be used to further your business goals.
Provide objectives and limits. Tell the candidate what you’re evaluating them on, how many hours you’d like them to invest (never more than 4hrs), the audience, and how you’ll review their work (presentation to a group, discussed 1/1).
Be prepared to match their effort! Have a rubric and evaluation guide for yourself ready to review the “homework” against. Prepare standard questions for follow ups that you’ll ask all candidates. Review their work prior before meeting again to discuss. Have thoughtful observations ready.
The task should match the role. If you’re looking for a Head of Talent to drive strategic initiatives and programs ask about how they build a strategy for X challenge. While you may ask a Recruiter how they’d build a sourcing strategy for a specific role or complete an intake meeting, this may not be the best use case for the leader of the function to showcase their skills.
And now you have a great starting point for hiring your Head of Talent. Happy hiring!
