September 11, 2025

It's Time for a Check-In

Happy Thursday!  Here’s what you need to know in tech in under 2 minutes…

 

What tech leaders should be thinking about this week:  Checking-in with each of your team members to see how they’re doing.  I know it sounds super-simple … asking your folks“How’s it going?”  But I think we’re at a time in our lives when a check-in is important. In February, I wrote about how you can set yourself apart when youanswer this question for yourself. But the other side of the coin is also critical – especially if you want to set yourself apart as a true tech leader. Winning in leadership is a combination of a setting a high bar and demonstrating deep devotion (thanks again Francis Frei). I’ve learned you achieve this by regularly checking-in and through different open-ended questions will ensure you don’t get the dreaded “Fine” as an answer. Some of my favorite questions include: What’s been your experience? How’s your temperature this week? Where are you struggling? When have you been at your best/worst?

Why this is important:  Checking-in is critical for one main reason:We are all humans. I’ve found that most of us in tech forget this – we’re too obsessed with the daily acronyms driving our business:  KPIs, OKRs, AI, QBRs, 1:1s, etc. A quick, open-ended question to your direct reports shows that you care about what impact they are delivering AND how they’re doing as a human (remember, it’s all about big results and tons of support). You force a pause in the daily grind and give your team members an opportunity to think about their experiences +ways to make it better (another reminder that you don’t need to solve their problems; rather be a sounding-board for potential solutions). Just the act of asking “What’s happening in your world?” can score major leadership points

Where you’ll see impact:  I’ve seen tech leaders win in two areas when you become more devoted to your team’s wellbeing. First, you’ll just feel better. Attention is shifted from the “what” to the “how/why” causing a decrease in stress/intensity. You’ll experience a lightness knowing you’re focusing on something other than the business (a human being). Second, the employee wins because they know they have a leader who cares about BOTH the “what” and the “how/why” creating more engagement and loyalty. While they are responsible for resolving any specific issues, having space to discuss their experience will make everyone’s job easier (and produce better results for the organization).  

Value Add – Additional ways to show-up as a leader:  I have another podcast that I think you should check-out!  The NewYork Times “The Interview” podcast spoke with Brené Brown this week and I think you’ll get a ton of value out of her 35-minute discussion.  Brown defines a leader as “anyone who holds themselves responsible for finding the potential in people and process and has the courage to develop that potential.”  She talks about how to make this philosophy come alive in today’s ever-changing(tech) world – something that’s really difficult … and achievable.  Check out the episode here or wherever you get your podcasts!

Need someone to ask you how you’re holding up?  For the last two weeks of September, I’m offering a quick 30-minute sync to anyone who might need a little devotion (or reality check) for free.  Sign up directly using my calendly link or forward this to a friend/co-worker who might benefit from some free “Tom Time.”  Hurry! This offer is only available for the last half of September.

 

Here’s to your Engaged Pursuit!

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