How to Hire Generalist Talent 101

Hey there – apologies for the late sending of this newsletter. Between playing Lacrosse, running a business, revamping a website and matching tons of candidates to startups, this fell short last week.

Today, we’re taking a look at the startup side of things: how to actually hire a generalist, what to look out for, and how to run the process.

Let’s dive in. 🤿

A few years ago, I took part in a cohort-based community called the “Operator Angel Collective”, where a bunch of former founders and/or startup operators who had made at least one angel investment got together.

The host, Felix, invited a bunch of experienced investors to teach us more about angel investing. My main two takeaways were:

1. I’m too poor for this s**t
2. “Picking” the right investment only makes up for ~30% of success in investing

I’m not gonna go deeper into the first aspect, but the second one is interesting.

Successful angel investing comes down to three aspects:

1. Deal Flow
2. Deal Selection
3. Deal Access

If you don’t see any deals, you can’t make an investment. So first, you need to make sure that deals come across your table.

If you don’t pick the right deals, you’ll lose money. Picking is a highly inaccurate science, but there are some indicators that allow you to screen out the bad ones. (Not going into detail here, this post isn’t about investing.)

But even if you see and pick the right deals, the founders still need to want you on the cap table. You need access. Better to have less investors than bad investors.

And we can apply this to hiring.

Let’s say you’re hiring for a Founder’s Associate position (or any generalist position, for that matter).

When I say “generalist”, I mean someone who can solve a wide range of business problems across functions, rather than specializing deeply in one domain.

Generalists are most valuable when problems are ambiguous. If the job is highly repetitive or deeply specialized, hire a specialist instead.

We’ll break down the process one by one: flow, selection, access.

Candidate Flow

First, you need to see candidates. Given the current situation in the job market, that shouldn’t be an issue. Post a job and lots of people will apply – arguably, too many will apply.

Most profiles will be bad and screened out.

Side note: this is statistically logical, as application quality doesn’t have a bell curve distribution, but is skewed massively towards “terrible”. The best candidate in the world likely has to write one application in their entire career (for their first job); the worst candidate in the world who never finds a job probably writes tens of thousands over the course of their career.

A few ways to generate candidate flow:

• Post job ads on job boards (primarily LinkedIn)
• Share your posting in communities with your target group
• Ask your network
• And, of course, work with companies like Generalyst

You probably wanna do all of that to maximize flow if you have infinite resources to screen. Otherwise, cut the job boards, as they tend to have the highest noise-to-signal ratio.

So far we’ve covered how to see candidates and how to evaluate them. Now comes the part many founders forget: getting the best candidates to actually join.

Candidate Selection

Evaluating generalist candidates is quite tricky. With salespeople or engineers, you can resort to skill-based hiring like “sell me this pen” or doing a coding review.

With generalists, this is more tricky – because you’re hiring for soft skills. You need communicators, problem solvers, rapid learners with a sound professional toolkit.

Ask any hiring manager, and they’ll give a laundry list of traits that all may or may not be relevant. But in our experience, it comes down to five factors:

1. Excellence → how you do anything is how you do everything; if they’ve found outlier success elsewhere in their life, they can probably reproduce it
2. Agency → you need people who think for themselves and offer solutions, not problems.
3. Communication → startups are messy enough already; no need to add a layer of confusion by hiring someone that cannot articulate their thoughts.
4. Bias for Action → you want someone who asks for forgiveness, not permission.
5. Startup Fit → they need to create playbooks instead of following them; corporate / VC experience is often more of a disadvantage than an advantage.

Identifying Talent

This is the tricky part. How do you test for this? Most hiring managers just look at CVs, see if they can recognize logos, and move on.

That’s a terrible idea. Soft skills often don’t stick out in CVs.

Instead, here are a few suggestions:

• First, accept that finding top candidates is difficult. Most of them don’t apply very often.
• Use video introductions (which we’re now implementing at Generalyst). They give you a glimpse of the candidate, how they communicate, and what they’ve done so far.
• Run a tight, disciplined interview process, where you dig deeper into their experience so far to find markers of the traits specified above. (We already do the first round of interviews for you at Generalyst.)
• Take a real-life problem and give it to them as case study (not just a hypothetical one). Work on it together with them; most generalists will work very closely with the founder, so how you collaborate will be an important factor. You can also test for their ability to quick grasp a new problem that way.
• Always ask for references, and call 2-3 of them.

Common Mistakes

Hiring for logos instead of signals

• Seeing McKinsey, Google, or a top university on a CV feels reassuring, but it’s a weak proxy for ability. What matters is what someone actually did: projects they owned, problems they solved, and outcomes they drove. Generalists often come from unconventional backgrounds where they had to figure things out themselves.

Writing vague job descriptions

• Many Founder’s Associate roles read like: “Work closely with the founder on strategic initiatives.” Sounds exciting, but tells candidates nothing about the actual job. Strong candidates want to know what problems exist, what they’ll work on first, and how success will be measured.

Expecting specialists to suddenly become generalists

• A high performer in a corporate role isn’t automatically a good startup generalist. Many specialists are used to clear processes, defined responsibilities, and stable environments. Startups are messy — generalists thrive in ambiguity while specialists often struggle with it.

Over-engineering the hiring process

• Some founders build hiring processes with five interview rounds, multiple assignments, and endless case studies. The best candidates won’t tolerate that level of friction and will simply drop out. For generalist roles, 3–4 steps with real conversations and one practical case study is usually enough.

Hiring for skill, not talent

• Founders often try to hire someone who can do strategy, execution, hiring, and operations all at once. That’s a unicorn hire - and probably doesn’t exist. Hire for talent, train for skill.

Not defining success early

• Generalist roles easily become a grab bag of random tasks if expectations aren’t clear. Before hiring, define what success looks like in the first 6–12 months. I’ve seen people let go after 3 months simply because expectations for scope of work weren’t aligned.

Candidate Access

Now that you’ve seen a lot of candidates, and evaluated the right ones, you still need to get them to want to interview with you (and, eventually, take the job).

This is where many hiring managers go wrong: they view the interview process as a one-way street, and forget that candidates are also evaluating the opportunity.

So just like you’d be critical of a candidate that shows up late to a meeting, doesn’t communicate proactively, or ghosts you … the best candidates will be critical of you if you do these things, too.

Regardless of the state of the job market, the best candidates will still have plenty of opportunities to choose from (we see this at Generalyst, too, where ~20% of candidates get ~80% of the offers).

A few more things you can do to convince candidates that applying at your company is a good idea:

• Layer in “sales conversations” into the interview process, where you sell them on why joining your company would be a great idea based on what they’re looking for
• Write an elaborate, honest job description that goes beyond bullet points. The more detail and authenticity, the better.
• Get an opportunity to pitch in front of a curated set of candidates. A 10-min pitch will drive infinitely more interest than any job description. (Generalyst allows you to do this.)
• Make a respectful, slightly-above-market offer with simple incentives. That shows appreciation for the candidate; there’s no bigger turnoff than a lowball offer.

Make the candidate want to work with you.

In Summary

If you remember one thing from this article, it's this:

Great hiring comes down to three things:

Flow → Selection → Access.

• See great candidates.
• Identify the right ones.
• And make them want to work with you.

That’s largely how I think about hiring.

Want me to go deeper on a specific aspect? Send me an email and I’ll add it to my backlog of things to write.

And that's it for today. Have a lovely week.

LFG. 🔥

Dominik

LinkedIn | Threads | X | Bluesky | Instagram | TikTok | YouTube

Whenever you're ready, there are four ways I can help you:

[1] Reclaim up to 4 hours per day and find time to do the things you've always wanted to do by enrolling into Personal Productivity OS.

[2] Hire your next Founder's Associate or other business generalist position with my startup, Generalyst Recruiting.

[3] You could also find your next startup job in Europe by simply applying as a candidate.

[4] Learn how you can build your career as a generalist by subscribing to this newsletter. ⬇️