Like a bawse! — What to ask when hiring executives

Startups are all about the capabilities of a team. A company is not the creation of one individual, but rather the outcome collective contributions of a small army. Hence, hands down the most important thing you do as a startup founder is hiring the leaders who are responsible for building their respected functional teams.

For many years I’ve kept an Evernote with best practices I read or hear about, encounter, and use when it comes to executive hiring. I’ve found myself sharing these notes several times with Creandum portfolio founders when they embark on these hiring processes, so I decided to publish the collection here summarizing the most important questions to ask when hiring an executive and some overall key learnings around how to manage the process. Much has been said on this topic before so I’d love to thank the many founders, co-investors, academic journals, books and team members who have helped me to learn and iterate on this topic. My ambition is to continue to absorb more learnings along the way and update this as we go along. Hence, if you have any amazing additions to this, feel free to send them my way. 🙏

Self-awareness and motivation

One of the most important personality traits in any human (not only executives) is self-awareness. By truly understanding yourself you can better understand others and the best leaders they understand the people they work with.

  • If you could change anything you wanted at your current employer which would cause you to cancel this interview and stay with your company, what would that be?> Look for a genuine understanding of the reasons to move to a new company, and ownership of the existing working environment.
  • How would this new job differ from your current job? > Make sure the person has deeply thought about the role and organization they are joining. Understand how they feel about the differences identified and what excites or worries them. Beware of those who think their experiences are immediately transferable, especially from big corporates.
  • Why do you want to join a small company? > Beware of equity as a primary motivation since one or two percent of nothing is still nothing. Look for those who aspire to create something vs managing a business.
  • Tell me about a project which failed and how you could have changed the outcome. > Any good leaders take accountability and own up to failures. you look for someone who understands they control the outcome and it’s not about what others do.
  • Tell me about a time in your career when you wanted something so badly that you were unstoppable pursuing it. What obstacles did you have to conquer to get there? > Startups are always hard and difficult journeys. Hence, look for leaders with tenacity and grit, and understand what drives that behavior in them.
  • Tell me about a professional area you are currently exploring and trying to grow within. How did you discover it? Why are you pursuing it now? What’s your plan to fill that gap? > All exceptional professionals continue to grow, be hungry to learn and refine their skills. Find the pursuit to grow and the reasons for it, but also look for self-awareness of their process into deciding what, how and when to learn.
  • If I spoke to one of your offlist reference, a person you would NEVER opt-in to connect me with. If you put yourself into that person’s shoes, what would that person say about you? What would be that person’s reasons be for me not to hire you? > Everyone of us has people in our past which professionally didn’t work out. Look for execs who understand their own weaknesses, own up to them, and work on overcoming them.

People skills

To lead people you need to be able to hire, develop, nurture and motivate talent. These are all key characteristics of people skills, which is probably the one most important functional skill you need to assess for in this process.

  • What do you look for in people working for you? How do you assess for that during the interview process? > There are so many cliches and one-liners (such as this entire blog post 🙃) when it comes to hiring practices, but the best execs know how to hire the best people and should be able to articulate a thoughtful approach with minimal guesswork behind it.
  • If you join here, who would you bring with you into the organization? > The best execs opens up access to additional top talent. Validate and confirm that this access exists.
  • How do you train people for success? What’s your process of evaluating them? > The best execs not only hire amazing people but also help them grow — a key area of any successful team over time. Again, this is where people easily can drop one-liners to sound smart, but you need to dig deep into the answers to get to the substance of their tactical approach.
  • How do you deal with chronic bad behavior from a top performer? > A classical doubled-edged sword in management. Try to understand how the person weighs operational results vs culture + team spirit. Often times there are no right or wrong answers but what you’re looking for are people who have maturity in their leadership to navigate these complex situations.


In addition to understanding themselves and the people around them, any good leader has to have a repertoire of “hard” management skills which serves them in their daily work.

  • What’s your process of decision making and what methods do you use to get the information that you need to make a decision? > Decision making is a key component in the role of any executive. Often times this is done based on information from others or without perfect facts. Get a sense of how systematic and thoughtful they are around this, and their abilities to articulate the rationale behind specific decisions made in the past with imperfect information available.
  • How do you systematically get information about the rest of the organization, your customers and the market? > Similar to above where the exec may not directly be exposed to all parts of the business. Look for people who enjoy moving between strategic and tactic topics. Startups need both!
  • Describe the key leading and lagging indicators for your current organization. What was the process you used to define and monitor them? > Get an understanding of how s/he is using data and KPIs in their management style and how that is balanced with the human element.
  • What will you do the first month on the job? > Any new hire always starts with an onboarding period — so also execs. But with senior hires, you’re actually paying for the experience. The best ones come with initiative and ideas and hit the ground running to implement those. Beware of someone who wants to focus entirely on “learning” as it indicates s/he thinks there’s more to learn than there actually is. Speed is everything in a startup and you want to bring in people who are excited to take action and charge.

The process

Hiring execs is something which should be done in a thoughtful and articulate way. You need a process and a framework, especially if you’re hiring senior professionals into a function you know very little about yourself.

  • Understand what you need by doing the job yourself. How do you hire a leader into a role you’ve never experienced or know anything about, say if you’re an engineer and want to hire a VP of Sales? The very best way to understand the requirements for any role is for the founder to act in the role. Not just in title but in real action. Before you start your executive hire process, act and learn about the role.
  • Don’t just ask open questions and listen to answers. Your aim is to go deep on the answers! Probe by asking for specifics, and dig by using who, what, where, when, why and how.
  • Define the strengths you need and weaknesses you are willing to accept. Do not think of this list as a role description. Instead, look at the list and develop questions that test for the strengths and weaknesses, and assemble an interview team who can help you best evaluate against these criteria. More often than not you’ll need to bring in external people to help you who have expertise in specific fields.
  • Hire for success today — not tomorrow. Look for someone who has the capabilities and experience from taking your business from where you are today to where you need to be in18 months from now. If you’re 10 people and want to grow to 60, look for that. Not someone who scaled a team from 100 to 1000 people. If you’re at $1m ARR and want to scale to $10m, look for that. Not someone who scaled a $100m business.
  • Optimize for strengths, not lack of weaknesses. Hire someone who is amazing at X rather than lacks Y. Nobody is perfect and any candidates will come with some weaknesses. Remember unicorns aren’t real. 🦄🚫
  • Don’t be consensus-driven. As a Swede, consensus is hardcoded in my source code, but when it comes to exec hiring the final decision should be made by the CEO. Consensus decisions about exec hiring almost always sway the process away from strengths and towards lack of weaknesses! Usually, the CEO is the only one who has the 360-degree picture of the situation and the rest of the team should trust their decision.
  • Reference and reference again. Always ask the candidate for front-door references. Any opt-in references will naturally be very positive, but use them to test and evaluate against the strengths and weaknesses you defined above. Also, do backdoor references. Plenty thereof.
  • Rapid Q&A onboarding. Schedule daily 1on1s with the new exec with the purpose to help them understand the business better. Put the person into the mix with key people and make sure they learn from them. Ask them to bring a comprehensive list of questions they have. High and low topics where all questions are welcomed. Answer them in-depth. If the exec doesn’t come with questions, consider firing them, and if s/he is not up to speed after 30 days, also consider firing them.
  • Show wins early. Make the new executive create and deliver as quickly as possible. The rest of the company is watching closely and expecting magic from this senior professional who brings a wealth of experience. It’s essential this person comes in and show “wins” to the organization. Help them with monthly, weekly or even daily objectives to make sure they produce immediately and make sure the output is visible to the rest of the org.

Finally, very little has been said above about hiring for culture, because that in itself is a topic worthy a separate post. Culture naturally plays a key part in any hiring decision. However, the one critical thing around culture and executive hiring you need to note is that when leaders join your organization you are fundamentally adding key decision-makers to your team. Any decision-maker will naturally influence the culture of your organization. This means with executives you should rather think about the “culture add” they will bring vs the “culture fit” they may have. 💪👊

Carl Fritjofsson

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