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Hiring an experienced non-technical leader when you haven't hired for one before

Updated: 5 days ago

More recently I've been speaking with early-stage companies which are going through what feels like a"growth" phase:

  • Everything feels like it is under fire

  • Everyone is overstretched

  • The people who are founders or act like founders are often impatient at the lack of progress the teams are making

I don't think there is much debate when it comes to hiring a senior technology leader like a CTO because unless there are structure and quality standards in what you are building then further down the line there will be barriers to growing. However, there is a healthy amount of ambiguity when it comes to hiring a non-technical leader say CPO/VP/Director/Head of Product/Customer/Operations.

Now every growth phase feels different, it's hard to compare one company's growth phase to another as every stage of a healthy company's lifecycle is built on growth however incremental. One solution which is often dictated by the board is "It's now time to think about scaling your team, you need to show that you can hire and retain a good number of VP's". If you read between those lines they really mean, "You come across as a young company or are first-time founders and you need some folks with more experience to make you more desirable to investors". In this post, I am going to briefly uncover how to validate what you truly need as an early-stage company.

Whilst the part about desirability is not untrue, one has to acknowledge what one wants from an experienced leader. For example, I once had the privilege of working with someone who was one of the founding fathers of a well-established big tech product, well-known in that space and a true executive hire. However I discovered in speaking to him that the contract provided to him was very specific, be the face of the company for pre-sales calls (e.g. add us to your LinkedIn and join the said calls), validate some IP and we won't use more than 15 hours of your time a week all of which will be pre-booked with a set agenda so you can prepare. Essentially a poster-executive we were hiring to win deals at that stage of the company's life, showing to potential customers we were working with one of the OG's. I can almost bet that if the same executive was hired at an early-stage company the expectations on what they can or can't deliver would be out of kin with the folks hiring them.

If you speak to a number of senior leaders, especially those who were brought in at that level it's clear that there is a misconception either around what they can and can't deliver and/or they often recall stories of companies where they were simply not needed. I haven't spoken to one senior leader who can't cite one or more examples in their career where this was not the case.

Wait Nik - you're contradicting yourself you said when I hire a senior product person I should be hiring someone who can almost be a chameleon. I did but even when I explained what to look for, the underlying theme was that whoever you hire needs to have tangible goals linked to the stages of the company to make them a successful chameleon, in reality you can't have a doer and a visionary at the same time for an early stage company. Also because it's likely that the vision is being formed by the founder or by the earlier members of the team based on what they see or have seen in the market they just don't know it.

Coincidentally I have never come across an early-stage company who have not been having the same debate internally but often the questions asked are more abstract than they need to be.

To help here are some questions experienced leaders would hope the internal teams would truly debate

  1. How many customers do we have? What does the team structure look like for a company in a similar space with a similar number of customers and a similar level of funding (hint: do some LinkedIn stalking). Note: Yes, every company is different and you should not compare apples to oranges but the whole reason for doing this is to just see how companies deal with similar challenges

  2. If you were able to clone the team members truly stretched would you be able to better achieve the goals? If the answer here is Yes, then think very very hard about why you need a senior leader

  3. Do you just need the senior leader to help hire/recruit <5 people aka "build a team"? Again if the answer here is Yes, then think very very hard about why you need a senior leader. Why would you need help recruiting less than 5 people? You and your fellow colleagues know what's best for the company in terms of profile and the needs of the company - you may not know what great looks or feels like for the role you are hiring for but you can get insights by asking around

  4. Are you truly willing to have a trade-off between needs that you are hiring an expensive resource in the hope they would evolve with the company? For example, if you are hiring someone as a leader but they have to act as a product manager for say 2 years then you have to accept it as would they. The expectation is that they evolve FASTER with the company because they have prior experience, so for instance, if we raise $10mil they could execute on hiring faster because they have done this in the past.

  5. Are you actually looking for industry knowledge which you currently don't have or an industry insight? In that case, either hire an industry expert or consult with one on specific areas and challenges. Note: Every industry feels hard but it's defining what hard really is, the greatest product executors I have worked with are the ones who are curious and break down the hard into manageable chunks they work through, they often haven't had prior experience to do this.

  6. Who owns the budget for the team you are looking to hire the senior executive for? If it's not going to be that individual then realistically you are not hiring them to scale the team or you are not confident they will realistically add value - bear in mind they are used to being budget owners

  7. What are the operational decisions you would want them to take if they were here today? For example, you don't need a senior hire to necessarily identify and drive changes like building iterations of functionality or building 0 to 1 functionality like say a messaging bot/tool. You may need a fractional/part-time hire to validate/coach through decisions but this is different.

  8. Why can't the existing person doing the role or the existing people (if the role is split) continue doing that role? What is the trade-off they are doing today? Is whatever item they are trading off less or more important? The reason for this question is that most OG product people were working developing software before product was a thing, they know that like themselves most folks started in a different role (usually customer-facing) which evolved into a product role.

  9. Do you need someone to look good in front of investors? Consider bringing on an advisor, interim or part-time senior exec to help fill that position.

  10. Have you considered getting someone to help in the interim? e.g. a contract hire. They would cost you more but it will be a lot less than the upheaval if a big-hitting hire does not work out and they would also help bring in some structure and spend time helping assess what the organisation truly needs, there needs to be an achievable agenda and timeline set by the interim or contract hire.

Likewise here are the questions to work through with whoever you choose to hire

  1. Here is some of the daily "work to be done" - how would you approach each piece of work? This is work that you know needs to be done as part of the role such as liaising with stakeholders, raising sprint tickets, and running sprints - the key thing to get into is for you to firmly visualise the tooling and approach they would take. For instance, if it's sprint tickets, how would they validate what needs to be done? How would they ensure engineers are brought into the loop? If needed ask a friend/experienced leader who is external to the company to be in on the interview.

  2. What do you think you would not have time to do? Here you are not looking for them to say "I won't have time to speak with X" but you are looking to agree as to what they realistically won't be able to achieve. It's likely they will say not sure - help them be successful by working with them on what they won't achieve. For example, help outlining what a week could look like for the first few months. One senior leader recalls, the greatest onboarding experience I had was with a seasoned founder who said: "I'm hiring you for the greatest value you will have which won't be till 9 months or a year from now, till then I want your help by working in support, customer and sales teams to understand how the business works so I just want you to be an operator in each of those roles". If you think about how critical product is to the business and how entwined product is, he was right the future of the product at that company needed that approach, there were already folks working within the product he needed a 5-year leader, in the end, he not only got a 7-year leader he got someone who he could rely on.

  3. Set the expectation on what they can achieve and by when - make sure you bring them into different roles before they deliver on their core function. For example, most chameleon hires have worked in sales, support, and customer functions and you often see them start as say CPO/VP product and often go to CPO + COO and in many cases become the CEO allowing one of the founders to be the chairman.

  4. Outline what decisions you have found hard to make and why. For example, if it's a trade-off decision what makes it so hard to make that decision? What are the key pieces you are missing to make that decision?

  5. Give them the keys to the castle, and give them the operating manual for success. More on that later on.

I leave you with this extreme example where the hired leader is clearly not a good fit for the role :) in an effort to spur you on to think hard about what you need and when you need a senior hire.

Getting the senior hire wrong

Hope that helps please let me know how you get along and if you have other questions I have missed out on the above. Good Luck and as always feel free to reach out if you think I can be of help.

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