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HomeEntrepreneurWhy Founders Are 'Generally Absymal' at Hiring

Why Founders Are ‘Generally Absymal’ at Hiring

If you think you’re good at hiring people, you’re probably wrong.

We have unusual insight into this. Coauthor Richard Hagberg is a psychologist and executive management coach who has worked with thousands of clients, seen inside of hundreds of businesses, and has collected 40 years’ worth of data. His experience has shown that hiring is one of those disciplines that, like marketing or design, many founders are convinced that they understand and are very good at. But recruiting is a full-time profession for a reason. Too many times, he’s met brilliant founders who fail to grasp what’s required to build a good team.

Coauthor Tien Tzuo can attest to that from the founder perspective. He is formerly the chief strategy officer of Salesforce. He came to Richard 15 years ago after founding Zuora — now a $1.7 billion company — because Zuora was scaling fast but turnover was high. Tien realized that as his company grew, he needed to grow as a leader.

Related: I Discovered the Power of Employee Engagement — and Never Looked Back. Here’s Why It Should Be a Top Priority for Every Leader.

All these years later, we’ve teamed up to offer other business owners some practical, data-backed advice.

Here is our 6-step guide to finding and attracting the talent that will take your business to the next level.

1. Recognize that you are not good at this.

Founders are generally abysmal at interviewing people. Some of them are standoffish at best, and downright robotic at worst. Many blatantly telegraph what they’re looking for: “Well, we need somebody who will do this and this. You’re like that, right?” They forget that, in interviews, they are there primarily to listen. Sometimes, candidates can’t get a word in edgewise.

Our advice? Stick to the facts and focus on understanding the candidate’s past behavior. Avoid vague hypothetical questions (“Let’s say you were in the following scenario…”). Interrogate lived experiences: Why did you do this project? Who did you work with? What was the actual versus expected outcome? What were the biggest obstacles? What was your organizational structure? How did you interact with your cross-functional peers? There are no right or wrong answers; you’re just trying to get a sense of the person by how they respond. Their character will reveal itself.

2. Develop a disciplined hiring process.

Build a disciplined hiring process that includes writing out a job description, sourcing candidates, interviewing, following up, and reaching decisions. Enrich it by soliciting and synthesizing feedback from multiple references: team members, board members, and shared contacts. Utilize data-driven hiring tools like personality testing to improve fit and retention. It’s human nature to seize on commonalities and shared experiences, but those affinities can often obscure competency gaps.

For example, Tien is maniacal about job scorecards to keep interviews focused on skills, knowledge, and experience rather than just whether you like someone. His scorecards are derived from detailed descriptions of what the role entails: its context, its objectives, its challenges, its scope, and what you need the person to be able to accomplish. For important roles, he writes around a half-dozen drafts: writing, leaving it for a day, rewriting. And the best candidates? When they see their final scorecard, their eyes light up. They get excited. They can see themselves in the role. They see the future of their own story and their own growth.

Related: What Most Employers Overlook That’s Costing Them Great Hires

3. Diversify the gene pool.

You need to reach beyond your own network. This is where your investors and board members can contribute, particularly for young founders. It marks the difference between essentially posting a classified ad (“Wanted: VP of Product”) and taking advantage of a range of experienced perspectives to locate a specific suite of skills.

You might also consider hiring a recruiting firm. Be careful, though, because a lot of these are glorified temp firms. Look for a company that invests in understanding not only the job specifications but the culture. They need to conduct a thorough search to find exactly what you need. Avoid the folks who are just dialing for dollars.

4. Hire for the team, not the position.

You can’t put together a good basketball team with five all-star forwards. But founders tend to hire in a silo. They want the best salesperson. The best engineer. The best marketer. And they wind up with a bunch of big egos who can’t work together.

At a certain point, you’re going to need more experienced people. The biggest problem is that these hires have developed clear models of the “right way” to do things. If they have spent a long time at a single company, they may try to simply repeat past formulas. They will likely be more balanced if they have worked at multiple companies at various stages of growth, and even better if they have different industry or market segment experience.

Someone coming from a big company presents another kind of challenge. If they were around during the growth and scaling of their last company, they may appreciate the lack of systems and processes at a startup. But if they joined at a more advanced stage, they could have real difficulty adjusting to the informal, unstructured nature of a startup. They may tell themselves (and you) that they will enjoy the challenge, but they tend to be thrown for a loop by the ambiguity and chaos. They label it as “naive.” As a result, your early employees attack them as “big company” people and don’t benefit from their scaled-up models and processes.

Related: Why Proper Hiring is the First Step to Team Success

5. Practice extreme back channeling.

Back channeling is incredibly important. If you can’t find information about someone through your own network, cold-contact people who used to work with them. Don’t ask fuzzy questions like: Would you hire this person again? or How was your experience with X? Focus on the details: What specifically did this person do? How did they work with other people? What challenges did they face? What specific outcomes did they generate? Just because they came from a successful company doesn’t mean they were in a role where they “made it happen.”

Why is this so important? Well, some people are very skilled interviewers. Marketers know how to tell a good story. Salespeople know how to pitch. Someone might dazzle throughout the entire process but be fundamentally unfit for the role. People who have worked with the candidate can tell you volumes. For example, you might get what Larry David calls a “non-recommendation recommendation,” in which an ex-coworker damns the candidate with faint praise. That’s always a red flag.

6. Ask yourself: ‘Am I buying or selling?’

Finally, interviews aren’t just about assessing candidates. They’re also about selling your company: the vision, the market, the funding, the product, the team. For experienced candidates, they have many options and weigh these fundamentals very carefully. They want to kick the tires.

Here’s a simple way to think about it: When you’re buying, you’re listening — and when you’re selling, you’re talking. You need to switch gears at some point: “Do you have any questions that I can answer?” Now is your time to talk. Leverage your vision to inspire someone. Let people know their creativity is valued. This is vitally important if you want to attract people who can tolerate ambiguity and risk, because it will give them the flexibility to be innovative.

Ultimately, hiring is both an art and a science, requiring vision, empathy, and analytical rigor. By recognizing your own limitations, leveraging external expertise, and building a structured approach, you can cultivate a workforce that not only drives results, but also bonds together in spirit and collaboration. You can build a team of happy warriors.

Related: The Leadership Practice That Dramatically Improves Employee Retention and Performance

This essay was excerpted from Founders, Keepers, copyright © 2025 by Richard Hagberg, Tien Tzuo, and Gabe Weisert. Reprinted with permission from Matt Holt Books, an imprint of BenBella Books, Inc. All rights reserved.

If you think you’re good at hiring people, you’re probably wrong.

We have unusual insight into this. Coauthor Richard Hagberg is a psychologist and executive management coach who has worked with thousands of clients, seen inside of hundreds of businesses, and has collected 40 years’ worth of data. His experience has shown that hiring is one of those disciplines that, like marketing or design, many founders are convinced that they understand and are very good at. But recruiting is a full-time profession for a reason. Too many times, he’s met brilliant founders who fail to grasp what’s required to build a good team.

Coauthor Tien Tzuo can attest to that from the founder perspective. He is formerly the chief strategy officer of Salesforce. He came to Richard 15 years ago after founding Zuora — now a $1.7 billion company — because Zuora was scaling fast but turnover was high. Tien realized that as his company grew, he needed to grow as a leader.

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