Almost all interviews should be a combination of evaluating and selling. In tech’s current market, supply is outpacing demand, and good candidates are evaluating multiple opportunities at nearly all times. Bait the hook. Prep for the interview and know your candidate before meeting them. Plan ahead so you can pitch them on what’s important to them, and extract the information that’s important to you. Feel free to start with an outline of what you’d like to cover, and leave room for them to ask their own questions. 

Make sure to clearly frame the role, and explain why it’s important to the business. Be forthcoming about business milestones, and candidly address business challenges you’re currently facing, particularly those they’ll be expected to tackle. Practice your pitch/overview with someone, either internally or better yet, someone external to the business that you trust who can give an outsider’s perspective. Make sure that the candidate is walking away with the conversation with a strong impression of the company, and of you! 

One of the most common and most valuable exercises is to take 20-30 minutes to walk through a candidate’s entire career in chronological order. Some people take longer depending on the granularity they want. Pay attention to why they made the moves they did and what they learned from them. Ask questions along the way - the list below can help guide your conversation. 

How did the company grow during their tenure (headcount, team, revenue, users - whichever are most important for their role)? 

Look for quantitative answers, and push for absolutes if they provide relative answers like “we grew 300% in revenue this year”. What was the metric when they joined and what was it when they left? 

What was their impact on that growth and change? 

Should be able to tie their responsibilities directly to the growth of the business, and should be able to articulate why they’re partly responsible for the outcomes of that company. 

If they’ve been through analogous growth to what you anticipate going through with them at the helm, spend more time on these questions in regards to that company or time period. What did they learn? 

Who did they report to, and who reported to them? 

This will help get a sense for how large an organization they were leading, the seniority of their role, and how their organization was valued internally. Have they managed managers? Have they thought critically about why their org was designed that way, and would they have done it differently if they could go back? 

How would their colleagues describe them? 

Ask them to address the way their viewed by their managers, their direct reports, their organization at large, and their peers in different functions. 

Their answer to this question may be different from the way they’ve characterized themselves, if that is the case push for their view on why. 

Their answer to this question will also hopefully provide insight into what they’re like from a culture perspective. Do you think they’d gel with their peers, their manager, and the people that would report to them? Beware of “culture fit” becoming “finding someone like you” - you’re trying to build a group of people who bring balance and different perspectives. 

What are some specific projects they worked on? What was the impact of that project and what were some challenges they had to overcome to achieve it? 

Search for work that is relevant to the things the person will be doing in the role you’re interviewing them for. How were they involved in the day-to-day dirty work of the task and how much of their time was spent delegating or managing? Look for detail. 

Why did they choose to join their last few companies? 

Good answers typically have to do with the people there, and personal growth and learning. An important quality in any startup leader is who they surround themselves with. 

Why did they ultimately leave their company for the next role? 

Look for internal motivations for personal growth and greater challenges. Do they stick through the completion of projects and leave once their job has been done, or run for the hills in the face of a challenge. Were their challenges centered around relationships, business problems, or otherwise? 

How does this role align with their career goals, or solve the challenges of their last role? 

Always drill in on short job stints ( < 2 years). What was it about their expectations of the position that changed and led them to leave? If they’ve been in the same role for a very long time, assess how they’ll adapt to a different culture and environment. This is particularly important if they’re coming from a large company. 

What would they have done differently in their last few roles? 

Why? Have they spent time reflecting on their mistakes and learning from them? Do they focus on what they could have done better with the hand they were dealt, or on external factors that were out of their control, or they didn’t have data on at the time? 

What trends do they see in their function or industry at large? 

Should be able to speak knowledgeably about the way their function is evolving and how their industry is changing. Have their past companies influenced the domain they were in, or did they take advantage of any trends? What is their view on the role their function should play in a company. 

Look for some excitement here, this is something they should have strong opinions on and a passion for. 

What point are they at in their job search? 

Are they opportunistically evaluating roles as they come along or actively planning to make a move? 

How are their other options pacing and do they need you to accelerate or slow down your process to fit their time frame? Never rush into a decision, but be malleable in how long it takes a candidate to get through your process.