Costly Mistakes in Building a Team
1) Filling the gap
Hiring only to fill a need results in missed opportunities and serious risks.
Picture a founder who believes their venture requires four key skills to achieve the near-term goals of the business, and their current team covers 3 out of 4. Their instinct is to hire for that one missing skill — no more and no less. This is common for leaders of early-stage ventures. Since resources are scarce, they don’t want to hire for anything more than they need. While this strategy makes sense in theory, it has pitfalls. When an early team is siloed and no member’s expertise overlaps with anyone else’s, there is little opportunity to push back on one another. Given the uncertainty and turbulence of a startup, this is dangerous. Early members of a venture need to be able to challenge each other’s assumptions. Otherwise, innovation is hindered and blindspots sneak in.
2) Waiting too long
If you start a candidate search only when you need the hire, you’re too late.
The impact of an early hire is incalculable. Great ones can shape a company’s future, while poor ones can unravel the entire venture. With so much on the line, entrepreneurs should constantly prospect for early team members, even if they aren’t ready to hire. Bringing in a key team member is like building a long-term relationship; the best are nurtured over time. If you begin your search only after your team is overworked and you have ample funds, you may feel pressured to rush into a major decision. To avoid that scenario, leaders of an early-stage venture should routinely network and evaluate new contacts as potential team members.
3) Over-engineering the job description
Job descriptions loaded with requirements may benefit a 500th hire, but undermine your 5th.
We’ve all seen job descriptions that list 10 or more prerequisites and numerous roles and responsibilities. These make sense for a well-defined job that has been filled by many individuals but that kind of job history doesn’t exist in new ventures so this type of job description shouldn’t either. Over-engineering a JD is problematic for a few reasons. First, it suggests a role that’s rigid. In real life, the role of each early hire is fluid. Every day is a new adventure. Second, it suggests that whatever a candidate did in the past will perfectly prepare them for their new role. That isn’t true either. Startups experience constant change, and so will each member of the team. Too many descriptions for these early roles suggest otherwise and attract candidates who aren’t the right fit.
4) Choosing skill over ability
With enough ability, skills will follow. But the reverse isn’t true.
In simple terms, our abilities stem from our nature while our skills are developed though learning and practice. The lack of a particular ability can make it nearly impossible to achieve a certain skill. I’ve yet to meet an elementary school athlete with a four-foot vertical leap; that explains why I’ve never seen one dunk a basketball. When the right abilities exist, a new skill can develop. Startup founders often overlook this. They hire for skill because they have an immediate need, but conditions often change for startups. And when they do, so can the skills required. If a team member was hired for their skill, there’s no telling whether they can adapt to a startup’s changed needs. But if that same team member was hired for their ability, adapting to change should come naturally.
5) Forgetting to sell
If the only pitch in the hiring comes from the candidate, you’re building the wrong team.
I’ve witnessed many interviews where the interviewer does 80-90% of the talking. The interviewee nods in agreement and feels like they got off easy once their hour is up. Entrepreneurs know to avoid this, but they often take things too far. They focus 100% of their time peppering the interviewee with questions and answer only a few themselves. While they may have done a good job assessing the prospect, they are usually surprised when the candidate turns down the job offer. This rejection shouldn’t be a surprise at all. Startups are risk-taking adventures, created by ambitious people. While the upside of these ventures could be huge, job security isn’t a key selling point. So when a candidate doesn’t feel the passion or see the vision, all that risk might not seem worth it. Don’t be one of those interviewers who likes to listen to themselves talk, but equally, don’t forget that candidates aren’t just pitching you; you’re pitching them.
6) Downplaying the unknown
Startups must cope with uncertainty. If you don’t address that reality in hiring, your team won’t be ready for the challenges ahead.
The best entrepreneur interviewers know how to strike a good balance between pitching and getting pitched. But sometimes they take their sales tactics too far. In their optimism and passion — especially if they’ve recently been pitching investors — they might make lots of declarative statements: “We will do this…. We will do that….” That kind of confidence is appealing, but when an entrepreneur doesn’t balance it with a dose of uncertainty, they aren’t painting a believable picture for a new hire. And they aren’t acting like a responsible leader. Circumstances evolve, strategies adjust, and tactics change. Unless a team member is prepared to face all those unknowns, they may be ill-equipped for the new venture.
7) Focusing on answers instead of questions
A candidate’s perspective on what they don’t know can be more important than their mastery of what they do know.
This mistake is an extension of “choosing skill over ability.” When an interviewee answers a question well, they are exhibiting skill or knowledge. They are sharing what they think. This is important, especially if that skill is crucial for the venture’s success. But when an interviewee asks a question that goes to the heart of a venture’s mission or challenges a key assumption, that’s different. They are revealing how they think. The ability to search for what’s hidden, to seek opportunities where none are obvious, and to discover blind spots is hard to teach. But a candidate may never be able to show this rare ability if their interviewer is relentless in posing questions. Give candidates this opportunity by turning the interview into a genuine conversation.
8) Worrying about titles
No title truly captures the role of a startup’s early team members.
I’ve seen a young company with a ten-person team that included five “Chief <something> Officers,” three “VPs,” and a couple “senior” executives to round things out. While this example is extreme, this silly pattern is common in early-stage ventures. I understand what leads a venture to do that. The first hire arrives with ability, skill, and influence. They get an important-sounding title that seems appropriate at the time. Then there’s no going back. Business cards are printed. In short order, the company appears to employ only managers and executives. I’ve cautioned founders about describing their ventures too rigidly and I’ve warned against crafting over-the-top job descriptions. A “title-heavy” team can hurt an early-stage venture in similar ways. When a team member’s label doesn’t accurately represent what they do, who they manage, and the flexibility of their role, it becomes a needless source of confusion.
9) Motivating with compensation
Money makes the world go round, but it won’t bring out the best in your team.
I believe compensating a team member less than they are worth is a bad idea. Even if you could negotiate for less, don’t. This can lead to resentment and underperformance. Simply put, it’s not good business for the long term. But many entrepreneurs extend this rule the wrong way. They assume if underpayment hurts motivation, then overpayment will lead to superior results. For some team members, this might be true. But generally, beyond a certain level of compensation, people are more effectively motivated by earned recognition, sincere appreciation, challenging projects, camaraderie, hope of advancement, organizational achievement, and opportunities for personal growth.
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