Soft-Skill Upgrades for Tech Leaders

We obsess over optimizing our tech stack and tools while ignoring the operator who runs it all. The result? An illusion of progress that tries to cover for a weak foundation. Self-improvement for tech leaders has massive compounding effects, both personally and across the entire org. Can you upgrade yourself?

While a coach accelerates progress, you can start on your own. Here are the three areas that matter most and that I’ve seen people improve on by themselves. For each, I’ll list practical changes you can make starting today.

Time Management: Same Hours, Different Results

The problem: We’re rich in calendar events but poor in outcomes. While tech leaders love to complain about not having enough time, at the end of the day, everyone gets the same 24 hours. That includes CTOs who somehow do get things done, people running governments, and CEOs of Fortune 100 companies. Are you telling me you have more on your plate?

Letting your team regularly slip through your fingers is a surefire way to realize in a year or two that you’ve been grinding yourself out with little to show for it.

The fix: Calendar Reset

  • Start by writing down your assumption on how you spend your time at the moment. What percentage of time in an average week goes into putting out fires, coaching, etc? Write this down.
  • Track your time for 2 weeks to see where it actually goes. Contrast this with what you wrote in the previous step. For many, this is like a plunge into an ice bath.
  • Reset your calendar. Treat it like a review of a startup that is going through a pivot. Strip down everything and add back what makes sense to break out of momentum.
  • Identify your constants (the non-negotiables), place them first, and let everything else work around them. Are there recurring meetings that can be turned into emails? Others that can be changed to recur less frequently or shortened?
  • Run regular personal reviews/retros to check where your time is going. Perform this calendar reset every quarter or so to remove accumulated cruft from your weekly routine.

Communication as Leverage

The problem: We talk to be understood instead of to create action. Don’t think you can just deliver all the correct facts dryly and call it a day. You’re speaking to fellow humans, not a compiler. Otherwise, you’ll end up isolated as a leader from the rest of your peers.

Tech executives who can communicate effectively turn into major influences on the company. They shift from being order-takers to equal peers in the executive team. They have more success influencing the company’s direction. They have more leverage. You can, too.

The fix: Intentional Communication

  • Start every communication by identifying the action you want to create. Put yourself in the other person’s shoes and articulate the discussion in a way that makes sense from their point of view.
  • To drive change, always consider the other person’s WIIFM (what’s in it for me). Each person views things differently, and you have to tailor your message to them.
  • Learn to update the company without putting people to sleep. Storytelling matters. This requires coming to these meetings prepared with the right notes and your main messages. Don’t dump all the data in a monotonous way. Try to shape it in a way that would be interesting.
  • Record yourself to catch your verbal glitches and weak spots. Whenever you provide updates, speak at an all-hands meeting, or give a talk, extract all you can from the occasion by getting it recorded and reviewing it. It can be very painful at first, but it’s amazing at making you aware of small things that might be harming your ability to come across without distracting/boring others.
  • Before critical conversations, prepare your hot takes and define your wanted outcomes. Don’t just wing it.

Decision-Making in Ambiguity

The problem: Drawn-out decisions silently kill productivity. Open threads pile up. Some decisions never even get approached because people have learned “it won’t work.”

Chronic decision-waffling is one of the biggest issues I see today. Many leaders think they can keep waiting till the perfect moment when they’ll know everything. The problem is that the moment rarely comes, and even when it does, it’s usually too late. By that point, you’ve missed the train.

The fix: Decision Hygiene

  • Spot all the decisions waiting on your desk. They’re hiding everywhere, like Slack conversations you keep as unread, your inbox, post-it notes, and, worst of all, those things you keep in your head.
  • Make a meta-decision for each: Will it be decided, and when? This is the decision before the actual decision. You’re getting on top of things and making the active decision of whether something even is worth addressing, and, if so, picking a date so you’re responsible and don’t let things slide.
  • Use frameworks to move faster. It doesn’t matter too much which you use, but pick something if you realize you’re used to letting things draw on. For example, consider reversible vs. irreversible decisions and options, or risk framing to assess how problematic something might be.
  • Build intuition through feedback loops. Document your decisions and review them in retros (solo or with others) so you learn with time.

Closing

These aren’t just soft skills. They’re leverage skills. The compounding effect is real. Start taking care of yourself.