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How to conduct effective due diligence when selecting a manager?
A guide on questions to ask before joining a team
Hey! 👋 I’m Archie! Welcome to my newsletter - The Rougher Drafts. Every week, I write about leadership, career advice, product, and technology. Among other things, I’m building The Breakout Space - a career accelerator for ambitious early-mid career folks. Subscribe to receive new posts directly in your inbox and support my work.
Due diligence is a trust-building exercise!
In the previous post, I shared my top three observation-based parameters to identify a great manager. In this post, I’m sharing my top questions to ask before joining a team and how to bring your manager along in your due diligence. It may sound out of place reading it in an environment like this where job offers are far and few! However, you can still apply some of these to your existing job, and remind yourself of this exercise when you finally land that offer.
Before joining a team, take the time to do your due diligence and ask for your manager’s help in that. You’re going to spend your valuable time here, so there’s no point rushing into a decision. Right before you join a new team is also the best time to ask questions, since no one expects you to know anything. They don’t read too much into your questions or have any preconceived notions about you or your knowledge. So, ask whatever you need to in order to fully understand what you’ll be doing and whether you’re a good fit.
You can only be so effective in doing this yourself in the background. So, you should bring your manager along into the process. Most great managers will be supportive and help you land a decision. However, once they’ve made an offer, they’re also incentivized to close the position asap. This may lead them to create a false sense of urgency and urge you to accept on a quick timeline. In a situation like that, recognize your bargaining power. Remember that they invested time and energy in finding someone qualified, they can wait for you to complete your due diligence. Talk to them respectfully, put in a sincere request, and proceed.
Here’s usually what I say,
“Hey manager, I’m excited about this opportunity due to <X reason>. I’d love to speak with a few people on the team to learn more. I understand the urgency, however, I see myself being here for at least <X years>. So, I’d rather take some time upfront instead of rushing through this. Is that reasonable?”
The Due diligence process
1/ Talk to other people reporting to your manager
Before joining the team, ask your potential manager to connect you with others on the team, so, you can learn from their day-to-day experience. Build trust with them, ask probing questions, and try to go a few layers deep beyond the “sell call”.
When I was joining a new team at Microsoft, I was backfilling a role. I asked my manager to put me in touch with the person leaving. I talked to them about the team, the org, everyone’s working styles, where they hit the wall, and what each executive cared about. Since they were leaving anyway, they didn’t sugarcoat anything. That due diligence helped me prepare and better understand the culture of the team and the context behind some product decisions.
2/ Look for signs of care, empathy, and psychological safety
I like to see signs of how much a manager cares about their team. When talking to their direct reports, I ask them about their experience navigating tough times with their manager.
I also look at the type of people they have managed before. For example, it is important for me to know if they have managed an immigrant before and that I will get the support needed in immigration-related matters. If they lack experience in managing immigrants, I want to at least ensure that they’re open to learning unique aspects of managing immigrants which involves extra paperwork, and an understanding of internal policies. Immigrants often need their manager’s support to make a case in immigration matters; and may have specific circumstances leading them to fly far back home in case of an emergency. I’ve been incredibly lucky to have the support of my previous managers. It was due to their support I was able to navigate the EB1A application process smoothly.
3/ Look at their track record and past experience
Ask your manager about the last time they promoted someone at least at your level, the average tenure of folks on their team, and the range of levels they have managed. Depending on the role, level, and company, it may also be worth asking about their experience of firing people on their team.
4/ Learn about their aspirations
A manager that will go places will take you places. Learn about their career aspirations and see if it aligns with yours. It is far easier to get the right support for your goals if your manager also has similar goals.
5/ Ask about quantitative metrics from internal surveys
Most companies have a periodic employee survey that rates the manager, team, and org. You can ask your manager how they scored in internal surveys, and what steps they’re taking towards improving. I haven’t ever asked any of my managers about this because the other indicators were enough to decide. However, there’s no harm in asking for this data if that’s what you need to decide.
Ultimately, you cannot evaluate people just on the basis of checklists. You’ll also develop a gut instinct about the person. Don’t discount that! If something concerns you, it’s best to directly address it with your manager rather than pinning your decision based on assumptions or a scorecard.
If you’ve found a great manager, express your gratitude and keep in touch with them! However, if are caught in a rut with your manager, understand what you can learn from this and make sure to do your due diligence the next time. If all else fails, don’t fall into sunk cost fallacy and move on.
If you have questions or thoughts on the topic, you can tweet them to me or send me a DM on LinkedIn! I’ll tackle reader questions each week (keeping your name and company anonymous), and hey, it’s free! 😎
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