Ask your Team the Important Questions

If you’re interested in technology strategy, you might already know Kevin Kwok.  He’s a former investor at Greylock Partners and writes deep dives on various products at kwokchain.com (don’t worry, the domain is a joke and was bought for him by a friend).

His most recent post looked at how Figma and Canva, two digital design startups, are taking on Adobe. If that sounds interesting to you then read the article in full, but we’re here for one paragraph at the very end where he talks about aligning employees on the purpose of a company or product.

As companies grow, two things are true: 

1. It becomes harder to make sure everyone has the same, coherent understanding of the most important parts of your business. 
2. It’s easy to underestimate this as a manager (particularly as a senior manager/board member) because you may have access to a more holistic view than the rest of your team/company.
   

It’s why managers often find themselves repeating the same stories about company purpose, or strategic objectives, or key product features to make sure everyone is on the same page.

Kwok has a useful tip which goes beyond that: 

“One exercise I’ve often found useful for CEOs to do with their co-founders and team is to ask an important question about the company—and see how much everyone’s answers differ. People are always shocked at how much they differ from even their co-founder. It’s natural to have differences and that doesn’t even mean either person is wrong. But these unexpected differences in how to think about the company are the underlying faultlines that make it difficult to synchronize as a company…”

Next time, rather than just repeating key points to your team, why not try asking everyone what they think the answer is to a fundamental question.  How do we retain customers?  What’s the most important thing we’re working on? What do you think is the biggest risk to the team right now? If you think people will be shy in open debate, you can always collect the answers privately over email/Slack. 

You may find the answers illuminating as to how aligned your team really is.  Even after all those times you’ve repeated yourself.