February 15, 2022
We’ve all been there – if you’re in a leadership role, at some point you’ll be asked to join a board meeting, and eventually you’ll be in a board meeting that doesn’t go as planned. No matter how well you’ve prepped,the random question will come up that catches you off-guard. Despite what you feel, board members are not trying to pick on you – it’s their job! (well, the part about identifying things that you may not be keeping your eye on) “Where’s the innovation – the projects that we’re working on for next year?” “Why aren’t we hiring faster?” “Have you considered outsourcing some engineering hires?” These types of questions can often derail the meeting; a 30-minute boon-doggle about how this other company they’re on the board of is better at hiring than you, or take the attention away from the story that you WANT to tell.
Despite the rough edges, these questions generally come from a good place. The board is trying to push the company forward and identify risks that might blindside you. They are supposed to challenge your way of thinking and how you’re structured. Remember, the board isn’t involved in the daily operations of the company, but they do have an invaluable high-level understanding of how other companies and engineering teams that have been in your situation and stage operate. The real scary part is that, when they ask these questions, they’re often not so subtly trying to determine if they have the right leader for the future.
So when we receive these tough questions, how should we respond? How can we set ourselves up to bounce back quickly or better yet, get ahead of them altogether? To help figure this out, I’ve compiled a list of questions that boards ask engineering leaders so that we can start to unpack the issues in play.
What are you going to be doing that is innovative this year? What’s the next big thing?
Unpacking this question:
Boards often see companies that lose momentum after a period of initial success. They’re trying to make sure this company stays ahead of it. It’s the law of nature, competitors will chase you, and they will copy you. Boards are worried about how you will stay ahead of it. When boards ask, they’re trying to push the company to stay innovative, ahead of the curve, so you don’t get outflanked. You have a job to keep the ball moving.
If you unpack this question a bit further, they’re actually subconsciously asking if you really are thinking of the future, and able to prioritize work that benefits the future.
How to respond:
You can often prevent this type of question entirely by having it prioritized and quantified and taking time to showcase some innovation. In your board meetings, I’d recommend breaking out engineering work into easy-to-digest categories with one of those categories dedicated to “innovation.” try sneaking in a quick demo or screenshot of things to come. To provide the proper context, you could also juxtapose this with categories like marketable features (for your go-to-market teams), customer support, and/or other work necessary to sustain engineering in the future. The bottom line is that you actually want to show and demonstrate your board firsthand that you’re investing resources into innovation..
Why do we spend so much time on customer work?
Unpacking this question:
The board is (not so subtly) worried that they have a services company; not a product company. They’re worried that if you continue this trajectory and 10x the customers, that you’ll have to 10x the engineering team. Boards (like CEOs) want marketable features and innovation that leaps you ahead of future competition. Remember, software companies are great companies because of leverage. Build it once and sell it a million times. If they’re asking this question, they may perceive your product as potentially too custom and not scalable (In this case – scale when it comes to business model, not ops/sec capacity)
How to respond:
Your customer work may or may not be too high, but this is the opportunity to talk through the work that you’re doing now to allow for leverage in the future. Maybe you’re focusing on feature work that will remove the customization from regular customer engagements. Heck, maybe this is WHY the next two quarters are light on marketable features. These are the stories that you need to be telling, ones that position engineering work in alignment with the highest-level business priorities. In reality, this is an opportunity to position yourself as forward-thinking, and quell any notion they have that you’re a reactionary engineering org.
How’s hiring going? Why is your headcount not growing when sales is growing? How are we getting to 100 engineers?
Unpacking this question:
These questions are grouped together because they communicate a similar concern: your board thinks your team should be growing faster. No matter how much hiring you’ve already done, they’re likely to continue asking these questions. In one simplistic framing, as long as revenue is growing, your engineering team should be too. They’ll ask you to push your teams to build more, move faster, innovate more, etc. And there will always be those that believe that the ONLY way to achieve these unicorn outcomes is to hire more engineers.
How to respond:
Like when we discussed CEO questions, we all know it’s important to hire when you’re given the green light to do so. You don’t want to lose the budget when you have it, and your executive team is going to expect certain outcomes associated with those hires.
That all said don’t forget that you should showcase the hiring you have done. It’s easy to forget to show head count growth when you’ve already hired the folks. As a hiring manager, the hard work is finding, evaluating and closing candidates. We forget as a leader we need to show our work – that it got done.
When are you going to triple the size of the team? Who are your directors?
Unpacking this question:
In the previous question, their perspective is that hiring equals growth. This question is about evaluating what your plans are to scale the team, and if you’re the right person to lead them during this phase when you should be scaling.
When they ask this, the board perceives your company to be at an inflection point, and they don’t want to miss the opportunity to capitalize on it and capitalize on it successfully. They passed the “we just need to hire more!” sidebar.. In a way, they’re evaluating whether you, as the leader of the team, have the right plan, mindset, and strategy to scale your engineering team in the future.
How to respond:
Talk about what the org structure going to look like as you grow from 25 engineers to 100, to over 300 engineers. Where will you need managers, team leads, and directors, and what will they be chartered with? In other words, show them that you are a leader that is thoughtful and growth and can scale the team in the future. You may already have a vision for your team as you approach certain hiring thresholds, but this question is signaling that you might be overdue to show them this.
Have your teams considered outsourcing engineering work?
Unpacking this question:
There could be a few reasons why they could be asking about this. Board members probably have seen other companies outsource or contract specific work. They may perceive this as having specific cost/profitability benefits, or they might think that it will help in the pace of hiring by tapping a different talent pool. Your job, the tricky part in answering this question, is to suss out what they perceive the benefits to be.
How to respond:
Outsourcing some work may or may not be right for your team at the time this question is asked. But you really need to figure out why they’re asking in order to address their concerns properly. Read the situation: Is the company behind on hiring or is it trying to manage costs – or a little of both?
Ask if they have any companies in their portfolio they could consult with on this. They’re likely to connect you to that engineering leader and then you can figure out what that board member perceived as beneficial.
The key is to articulate that you know the perceived benefits of outsourcing certain engineering work, and you’ve considered that approach. Show your work and communicate why you’ve made the decisions you have. Frame why outsourcing engineering work will help or hinder your team’s ability to achieve business strategic objectives.
Conclusion
In hindsight, you’d love to get ahead of the questions the board will ask, but that’s not always possible. Unfortunately, there’s no one size fits all answer for the toughest questions you’re going to get. But the key to getting ahead of these questions altogether, or addressing them properly afterward, is to have a deeper understanding of why your board is asking in the first place. Once you understand “the why” behind the ask, you’re immediately better prepared for these moments.
