What Every Founder Should Know About Getting a Hire Wrong

By Tovah Paglaro

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Tovah Paglaro is a two-time founder, consultant, and advisor. She built and exited Avalanche Insights and Fathom AI (now part of QuestionPro), and now works with early-stage companies and organisations navigating growth and AI transformation.

Watch or listen to Tovah’s recent interview for the Founders and Leaders podcast series here:

One of the most universal lessons I’ve picked up across 20 years of building organisations is that, at some point, you’re going to get a hire wrong.

But I’ve come to think that “bad hire” is actually the wrong way to describe what happens.

Especially early on, you may be hiring for a role you don’t fully understand yet. You may be asking someone to reproduce something that works because you’re the founder. Or you may simply not know what that person needs to do the job well.

I’ve learned this one the hard way.

I Didn’t Know What I Didn’t Know

When we started building the platform components of Avalanche Insights, the really techy parts of the organisation, I needed to hire our first product manager.

I thought I knew what product was and that I could hire well for this role. I was wrong.

Now that I do know the product, I can tell you with certainty that I didn’t before. And we weren’t ready to hire for it.

We brought on a wonderful person who did his very best to help us do a good job. But I didn’t know what information he needed, or what systems and structures he needed around him. Nor did I know what the right product manager archetype was for an organisation at our stage, building the way we were building.

And because I didn’t really understand the problem, it took us a long time to recognise what needed to change. We kept trying to make it work, providing our new product manager with feedback and input. But the challenge was more fundamental: a misalignment between our stage and the expertise we needed.

It was a really frustrating experience for him, and his frustration was my learning.

I wasn’t prepared enough to hire well; I didn’t move fast enough when I made the wrong hire, and I didn’t know what I didn’t know.

The Responsibility Is the Founder’s

As a founder, you learn more about yourself than you can in almost any other working relationship. You learn how you show up when things are good and when they are bad. And all of that radiates out to the organisation.

When you make a big mistake as the founder, the people who pay for it are often the ones on the other side of that mistake. Not systems, not spreadsheets. People.

That’s why I think the responsibility sits with the founder. You need to understand what problem you’re actually hiring someone to solve, what kind of person can solve it at your stage, and what they’ll need from the organisation to do the job well.

Set People Up to Do Their Best Work

I learned another version of this early in my career, working in film and television production.

No industry is better at trusting people to do their jobs than TV and film. When you’re on set, everybody knows exactly what they’re supposed to do in service of a vision, and is empowered to do their job well. If they don’t do their job well, the consequences are pretty clear. 

You can ask people to do extraordinary things when they know what they’re responsible for, have the tools and information they need, and are trusted to do their jobs.

Good leadership means creating the conditions for people to do great work, including clarity about the work, trust in the person doing it, and the right structure around them to give them a real shot at excellence.

Sales Hires Expose the Problem Quickly

I’ve seen this play out in a very specific way with sales hires, and I know a lot of founders in the research and insights space will recognise this.

The systems and structures that enable founder-led sales are really different from those that support your first sales hire or sales team. When you’ve been selling as a founder, you have context, relationships, credibility, and a deep understanding of the product that a new salesperson simply doesn’t walk in with.

Much of that knowledge lives in the founder’s head. And if you haven’t built the systems to transfer enough of that context to a new salesperson, they can fail before they’ve really had a chance to succeed.

That’s a big reason sales hires fail, and again, it’s on the founder, not the hire.

What Should You Do When a Hire Isn’t Working?

You’re going to make mistakes. The question is what you do when you realise you’ve made one.

Do you take responsibility for the fact that you didn’t know how to hire for this role well? Do you support the person in finding their next role? Do you give them good recommendations and compensation on the way out?

Perhaps most importantly, do you let them go as fast as possible so that they aren’t being tortured in a role they aren’t suited for or prepared to succeed in?

Nobody benefits when that drags on. The person isn’t thriving, and you aren’t getting what you need. So let them get on with what’s next.

That sounds hard, and it is. But it’s also the kindest thing you can do.

Get Advisors Earlier Than You Think You Need Them

One thing I wish I’d done differently, in both Avalanche and Fathom, is bring in more external advisors earlier.

We had really good investors who also served as advisors, and that was valuable. But we didn’t outsource advisory support as much as I honestly now would if I were building in a new sector for the first time.

If somebody had been there to say, “The way you’ve set up sales is fabulous for you and absolutely going to kill your first sales hire, so let’s make some changes before you do that“, I would have saved a lot of pain.

Not just my pain, but that of the person on the other side of that mistake as well.

How Handling a Hiring Mistake Builds Trust

When you make a hiring mistake and have to let someone go, everybody in the organisation is watching. They have their eye on whether you show up with accountability, let that person go when it’s clear it isn’t working, and hire the right person.

They’re also watching whether you do it in a way that respects the person involved and takes responsibility for the fact that you just didn’t know what you were doing quite yet.

What you do in those moments tells people a lot about what it will be like to work with you when things get hard.

What I Measure Now

After 20 years of leadership across a whole bunch of different organisations, I’ve had a big shift in how I think about success.

As a younger person, I measured it by accolades, money, and wins. Did I get the hire right? Did we crush the metrics? Did we land the contract?

I don’t anymore. Or at least not exclusively.

Now I measure my success in the success of the people I get to work with. Are they doing their best work? Have I done everything in my power to make sure they can and are?

Sometimes that means they work with us for a decade; other times it means being the loudest cheerleader as they go on to crush whatever’s next in their career path.

One measure of leadership I’m particularly proud of is the people who came through the organisation, what they went on to do, and whether they can look back and feel that we helped them get there.

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