15 Mistakes Startups Make When Building Their First Engineering Teams

This is a recap of our discussion with Pedram Keyani, former Director of Engineering at Facebook and Uber, and our newest Visiting Partner. Keep an eye out for Pedram’s upcoming tactical guide diving deeper into these concepts.

Watch the full talk at pear.vc/speakers and RSVP for the next!

Mistake #1: Not Prioritizing Your Hires

The first mistake managers encounter in the hiring process is not prioritizing hires. Often, when faced with building a company’s first team, managers tend to hire for generalists. While this is a fine principle, managers must still identify what the most critical thing to be built first is.

“The biggest challenge that I see a lot of teams make is they don’t prioritize their hires, which means they’re not thinking about: what do they need to build? What is the most critical thing that they need to build?”

Mistake #2: Ignoring Hustle, Energy, and Optimism

People naturally prefer pedigreed engineers — engineers that have worked at a FAANG company, for example, or engineers that have built and shipped significant products. But for young companies that might not have established a reputation yet, they’re more likely to attract new college grads.

“They’re not going to know how to do some of the things that an engineer who’s been in the industry for a while will do, but oftentimes what they have is something that gets beaten out of people. They have this energy, they have this optimism. If you get a staff engineer that’s spent their entire career at—name-your-company—they know how to do things a particular way. And they’re more inclined to saying no to any new idea than they are to saying yes.”

So don’t worry too much about getting that senior staff engineer from Google. Often, bright-eyed, optimistic young engineers just out of school work well too. 

Mistake #3: Not Understanding Your Hiring Funnel

Managers must be aware of how their hiring funnels are laid out. No matter what size of company or what role, a hiring manager must treat recruiting like their job and be a willing partner to their recruiters.

Get involved as early as sourcing. 

“If they’re having a hard time, for example, getting people to respond back to their LinkedIn or their emails, help put in a teaser like, ‘Our director or VP of this would love to talk to you.’ If that person has some name recognition, you’re much more likely to get an initial response back. That can really fundamentally change the outcomes that you get.”

Mistake #4: Not Planning Interviews

Once a candidate gets past the resume screen to interviews, that process should be properly planned. Interviewing is both a time commitment from the candidate and from the company’s engineering team. Each part of the process must be intentional. 

For phone screens, a frequent mistake is having inexperienced engineers conduct them. 

“You want the people who are doing the phone screens to really be experienced and have good kinds of instincts around what makes a good engineer.”

For interviews, Pedram suggests teams have at least two different sessions on coding and at least one more session on culture. 

To train interviewers, a company can either have new interviewers shadow experienced interviewers or experienced interviewers reverse shadow new interviewers to make sure they’re asking the right questions and getting the right answers down.

Mistake #5: Lowering Your Standards

Early companies can encounter hiring crunches. At this time, hiring managers might decide to lower their standards in order to increase headcounts. However, this can be extremely dangerous. 

“You make this trade off, when you hire a B-level person for your company—that person forever is the highest bar that you’re going to be able to achieve at scale for hiring because B people know other B people and C people.”

What about the trade-off between shipping a product and hiring a less qualified teammate? Just kill the idea. 

“At the end of the day, these are people you’re going to be working with every day.”

Mistake #6: Ignoring Your Instincts

Failure #5 ties into Failure #6: Ignoring your instincts. If there’s a gut feeling that your candidate won’t be a good fit, you should trust it. 

“The worst thing you can do is fire someone early on because your team is going to be suffering from it. They’re going to have questions. They’re going to think, ‘Oh, are we doing layoffs? Am I going to be the next person?’” 

Mistake #7: Hiring Brilliant Jerks

During the hiring process, managers may also encounter “Brilliant Jerks.” These are the candidates that seem genius, but may be arrogant. They might not listen, they might become defensive when criticized, or they might be overbearing. 

The danger of hiring brilliant jerks is that they’ll often shut down others’ ideas, can become huge HR liabilities, and won’t be able to collaborate well within a team environment at all. 

So when hiring, one of the most important qualities to look out for is a sense that “this is someone that I could give feedback to, or I have a sense that I could give feedback to you.”

Mistake #8: Giving Titles Too Early

Startups tend to give titles early on. A startup might make their first engineering hire and call them CTO, but there are a lot of pitfalls that come with this.

“Make sure that you’re thoughtful about what your company is going to look like maybe a year or two year, five years from now. If you’re successful, your five person thing is going to be a 500,000 person company.” 

Can your CTO, who has managed a five person team effectively, now manage a 500,000 person team?  

Instead of crazy titles, provide paths to advancement instead. 

“Give people roles that let them stretch themselves, that let them exert responsibility and take on responsibility and let them earn those crazy titles over time.”

Mistake #9: Overselling The Good Stuff 

When a team’s already locked in their final candidates, young companies might be incentivized to oversell themselves to candidates—after all, it’s hard to compete against offers from FAANG these days. But transparency is always the best way to go. 

“You need to tell a realistic story about what your company is about. What are the challenges you’re facing? What are the good things? What are the bad things? Don’t catfish candidates. You may be the most compelling sales person in the world, and you can get them to sign your offer and join you, but if you’re completely off base about what the work environment is like a weekend, a month, and six months in, at some point, they’ll realize that you are completely bullshitting them.”

As Director of Engineering at Facebook, Pedram made sure to put this into practice. After mentioning the positives and perks of the job, he would follow up with “By the way, it’s very likely that on a Friday night at 9:00 PM, we’re going to have a crazy spam attack. We’re going to have some kind of a vulnerability come up. My team, we work harder than a lot of other teams. We work crazy hours. We work on the weekends, we work during holidays because that’s when shit hits the fan for us. I wouldn’t have it any other way, but it’s hard. So if you’re looking for a regular nine to five thing, this is not your team.” 

Make sure to set expectations for the candidate before they commit. 

Mistake #10: Focusing on the Financial Upside

Don’t sell a candidate on money as their primary motivation during this process. 

“If the key selling point you have to your potential candidate is that you’re going to make them a millionaire you’ve already lost.”

Instead, develop an environment and culture about a mission. Highlight that “if we create value for the world, we’ll get some of that back.”

Mistake #11: Getting Your Ratios Wrong

Companies want to make sure that they have the right ratio of engineering managers to engineers. Each company might define their ratios differently, but it’s important to always keep a ratio in mind and keep teams flexible.

Mistake #12: Not Worrying About Onboarding

Once a candidate signs on, the onboarding process must be smooth and well-planned. Every six months, Pedram would go through his company’s current onboarding process himself, pretending to be a new hire. This allowed him to iterate and make sure onboarding was always up to date. 

“It’s also a great opportunity for you to make sure that all of your documentation for getting engineers up to speed is living documentation as well.”

Mistake #13: Not Focusing on Culture

Culture should underscore every part of the hiring process. It can be hard to define, but here are some questions to start: 

  • How does your team work? 
  • How does your team solve problems? 
  • How does your team deal with ambiguity? 
  • How does your team resolve conflicts? 
  • How does your team think about transparency and openness? 

“Culture is something that everyone likes to talk about, but it really just boils down to those hard moments.”

Mistake #14: Never Reorganizing

Failure #14 and #15 really go hand in hand. As many companies grow, they may forget to reorganize. 

“You need to shuffle people around. Make sure you have the right blend of people on a particular team. You have the right experiences on a team.” 

Again, keep your ratios in mind.  

Mistake #15: Never Firing Anyone

Lastly, and possibly the hardest part of hiring, companies need to learn to let people go. 

“People have their sweet spot. Some people just don’t scale beyond a 20 person company. And, you know, keeping them around is not fair to them and not fair to your company.”

How To Actually Be Helpful to Early-Stage Founders

This post is an excerpt from longtime startup mentor and Pear Operating Partner Touraj Parang’s onboarding session for Pear Accelerator S20 mentors — handpicked industry experts who we personally match with each founder in the cohort. Interested in being a mentor? Reach out!

Build the Foundation: Get to Know the Team On a Very Personal Level
Establish a Heartbeat
Be a Good Coach and Look to the Future

By now, “let me know how I can be helpful” is such a cliched offer to founders in Silicon Valley that it’s become a Twitter meme. Being helpful to founders is often framed as a means to “network” in the Valley, or to become a successful angel investor, but the best mentors, like Touraj Parang, do it out of true love for the founder journey.

Touraj began “mentoring” as an entrepreneur in the mid-2000s via getting together with other entrepreneurs and sharing best practices. After selling his startup, he began angel investing, and being helpful was a natural thing to do for the founders he invested in. Over time, he shifted to simply advising without investing for the love of it.

“I personally like to know: what are the latest technologies or what are people thinking about? How are they trying to solve these tough problems? I take satisfaction in being able to help other entrepreneurs achieve their dreams, paying it forward. Lots of people mentored me and helped me, and so I feel like that’s the way Silicon Valley works.”

Especially at ground zero, companies can barely look like companies. It’s a different ballgame from mentoring more advanced companies. Touraj draws on his hard-earned years of wisdom to share best practices for mentoring founders at the earliest stages of a startup.

Step 1 — Build the Foundation: Get to Know the Team On a Very Personal Level

Most early-stage founders are struggling to answer very similar questions or challenges:

How do we grow the team? Who do I need to hire? What do I look for in a new hire? Is it how much culture matters? How much of a stickler should I be about culture if I need someone now?

How do we find that product market fit? What is really even my core value proposition? Who is my customer? Do I sell to bigger customers and a more expensive product or to smaller customers with a cheaper product?

“A lot of these questions are very much existential. It’s just picking a direction and not knowing which way to head,” says Touraj.

Fundamentally then, mentoring an early-stage entrepreneur is almost like being a therapist. Your role is to help founders figure out what their values are and who they want to be in the context of their company.

There’s no right answer to these questions, and that’s why it’s so critical to know the team on a very personal level.

So, before you even get into the idea, the market, the competitive landscape and all the other fun things about the business you’re working with — really get to know your founders.

“You really want to try to see the world as much as you can from their point of view. Because then you can actually help put things in a language that they understand or motivate them in a way that they would really click with it.”

What is their background? What have been some past challenges or extraordinary achievements that they have had? What are their personal aspirations and ambitions? Try to probe into their areas of strength and what they consider to be their weaknesses, individually and as a team.

Understand what success looks like to your mentees. Capture their initial goals, even if they are vague, and start from there. Though many similar challenges come up with early stage founders, the founders themselves are likely all very different.

“I try to level set initially and understand, ‘Where are they coming from?’, and then be responsive to where they are, and meet them where they are, rather than just having uniform advice for everybody. I try to be very mindful and personalize the guidance I give.”

Step 2 — Establish a Heartbeat

Part of building a solid personal foundation with your mentees is to establish a rhythm of the relationship. Whether it’s a weekly or biweekly meeting, put it in the calendar right off the bat. Hold that slot in your calendar and make sure your mentees put it in their calendar and stick to it.

Once everyone gets busy, it can be very easy for the weeks to go by and lose that thread. While it’s understandable that the meeting may need to be moved occasionally, do all you can to hold your mentees accountable to showing up for the meeting, and make sure that you do your share and stay available as well.


Once you’ve established the basics, the key skill to being a successful mentor is to be patient and practice being an active listener.

Active listening to me is not only hearing what the person is saying, but then asking questions to get to the deeper layers of what they’re struggling with,” says Touraj. “It’s engaging in a dialogue and withholding advice until you understand the root cause and what the objective is that you’re trying to achieve in that conversation.”

When a founder first comes to you with a complaint about a situation, the root cause of that complaint is often not clear. Sometimes founders struggle because they’re not clear on what goal they need to achieve. Sometimes they know their goal, but they don’t know how to achieve it. Some founders are very detail oriented but have a hard time of going higher up and looking at the big picture. Some founders are so academic and big picture that they don’t really see the operational steps necessary to get where they want to go.

You want to create a space for open dialogue so that you can get a clearer picture on the situation.

Get into that mode of investigative work. Part of that is nudging them by asking probing questions.”

Some example questions Touraj suggests:

  • What do we learn from this outcome?
  • What hypotheses are we trying to validate?
  • Are there other solutions to the same problem?
  • What you’re putting your efforts into — is that the highest priority?
  • Do you have resources to be successful? If not, what do you need and in what order?

Note that through all of this, your role is NOT to tell your mentees what to do. Remind yourself to address the assumptions, rather than making assertions. Try to stay away from ‘You need to go do this.’

“It’s good for founders to know your role is not to provide answers, but to be a thought partner, to be a sounding board. Let them draw the conclusions. Once you clarify the assumptions and the goals, they can come up with how to get there and sometimes they come up with it much better than you could.”

If the founders are hitting roadblocks or feel stuck, a helpful approach is to suggest options. You might say, ‘In other companies I have seen, these are some of the things that others have tried. Which one sounds good to you?’

Touraj notes that newer entrepreneurs can be hesitant to open up about their problems.

“They feel like because Pear is an investor or potential investor in the next round, they always have to give the happy talk and seem confident,” says Touraj.

“You have to make them comfortable and say ‘Look, it’s okay. It’s okay if you have challenges. We have all had challenges, and it’s actually a good sign that you have challenges and you’re seeking help, rather than trying to white-knuckle it and then fail.’ They need to feel that they’re not being judged in any way, and that really, as a mentor, you’re here to help, you’re not a secret agent of the VC firm.”

Step 4 — Be a Good Coach and Look to the Future

When you’re working with early-stage founders, remember that you are also working with future leaders. As such, for maximum impact, go beyond the therapist role and take on a coaching mentality.

“It’s about seeing what skills we can give them, so that they become great entrepreneurs and leaders as their startup grows. I try to encourage a lot of reflection and self improvement,” says Touraj.

One way to do this is to train your mentees on best practices that you have found useful in your own life or in the organizations you have worked in. Although Touraj was an entrepreneur, many of the processes and frameworks he shares come from his experience at larger organizations like GoDaddy.

Touraj also works to hold his mentees accountable to their own goals.

“When we are meeting, I always make a point of writing down every goal, or every statement they make saying that they will go and do certain things. In my next meeting, I refer back to those and make sure to see whether they were done and if not, why not, so that they get this habit of accountability — if they say something, if they commit to something, they’ll follow through with it.”

In setting their own goals, however, founders may not be stretching themselves or taking enough risk. A good coach will figure out exactly how far they might need to push a founder. The best coaches help their protégés achieve things they didn’t know they were capable of.

“I think one of our jobs is to encourage founders to be bold, to experiment. And that it’s okay to fail and to learn as long as you learn from it.”