Managing Top Performing Tech Talent

10 Techniques for CTOs to Leverage to Cultivate Their A-Players

👋 Hello Technocrats!

I wrote this article last year and it got a great reception. And since we’ve grown in leaps and bounds here at Technocratic I’m bringing it back for readers that may not have seen it before. I’ve also spruced it up in spots that needed clarity or more brevity. Hope you enjoy!

Cheers & keep the shark swimming! 🦈

Bobby

The key to explosive organizational success for the best CTOs is managing their top technical talent in the right way.

This is of course, easier said than done.

Top performers in the technology world can be mercurial, frustrating, contradictory and yet brilliant people who can change the game for your company.

They usually thrive in complex problem-solving environments & are driven by intellectual goals that are frequently difficult to capture or explain.

Managing tech talent can be very different from managing sales people, for example, and for good reason: technical work is not as cut and dry as closing a deal with a customer.

Additionally, a lot of technical work doesn’t directly tie into business objectives — which makes things even harder for the CTO.

In fact, managing top performers is possibly the most difficult job a CTO has to do.

But CTOs that know how to maximally leverage their A-players can often rise to the very top of the field.

Let’s look at 10 techniques the best CTOs use to manage their A-players.

10 Techniques the Best CTOs Use to Manage Top Talent

Let them Break the Rules (Sometimes)

Top technical talent doesn’t really play by the rules. You’ve got to realize this right away if you want to harness their potential.

Top engineers got to the top by doing things differently and if you want them to remain on your team you’ll have to continue to foster this rebellious attitude.

I’m not saying let them deploy on Fridays nights, but some amount of rule breaking will have to be allowed if they are to feel free to create.

Let me give you an example: I had set a mandate once that we were going to do our APIs in a certain way and everyone had to follow it.

One of our top engineers was adamant about changing building a new customer API completely differently. He was so good that I decided to agree & see what he came up with.

His API was a total hit with customers & we ended up adopting his new standard across the board. So letting him break the rules really paid off.

I wouldn’t recommend allowing top performers to break the rules often, but every once in a while it’s quite necessary, actually.

Give Them Unstructured Time

Engineering is so creative that top performers really need a certain amount of guaranteed unstructured time to ideate, research and just explore their imagination.

If you’re too regimented and strict with work allocations and you have no buffer, then top engineers will start to resent the work.

Unstructured time doesn’t have to be pie-in-the-sky stuff, though. It can be useful work that helps the team and company.

But it does have to come from the engineers own mind and they have to care about it / be passionate about working on it.

Meaning, it can’t be forced.

Google famously gave their engineers a certain percentage of personal project time each month.

This is a great for retaining and managing top tech talent (as long as you tie these projects back to the needs of the company.)

Don’t Always Promote Them

Sounds weird, right?

But as soon as you start talking to a top engineer about getting promoted what starts running through their heads is a lot of unnecessary paperwork, meetings and people headaches.

Some top performers just want to build tech. That’s it.

As a CTO that might be strange to you because you obviously got promoted to more managerial positions running teams and dealing with people problems.

But not everyone wants that.

So be careful to not automatically promote top engineers to management positions and ruin their effectiveness and happiness.

Instead find other ways to recognize and move them up the ladder.

For example in several organizations I’ve been a part of I created 2 career tracks: one management and one purely technical.

That way any engineer who just wants to build tech could do that while getting raises and better titles along the way just like anyone else.

If you don’t have this set up I suggest getting it going soon.

Give Them Enough of a Voice on Business

Top engineers don’t necessarily want to run the company, but they do want to feel like they understand where it’s going—and they want their work to matter.

The mistake some CTOs make is either keeping their A players totally in the dark about the business strategy, or overloading them with business context they don’t need.

The right balance is just enough business insight to help them connect their work to real-world outcomes.

Here’s how to do it well:

• Give them high-level goals and let them figure out the execution.

• Show them customer impact (data, feedback, etc) so they see their contributions in action.

• Ask for their perspective on tech-related business decisions, but don’t turn them into armchair executives.

Engineers don’t want to sit through endless slides on “go-to-market strategy.” But if you make them feel like their work moves the needle, they’ll be far more invested.

Encourage Breaks to Recharge

The grind mentality is ingrained in top engineers but it truly isn’t sustainable, so be careful how much you lean into that as a CTO.

The best engineers work in bursts—high-energy sprints followed by periods of recovery. This is true no matter how hardcore about hours the A players might seem to you.

If you don’t encourage them to take breaks, they’ll burn out. And once that happens, they check out mentally long before they actually quit.

Here’s what works:

• Encourage deep work—give them uninterrupted focus time, then let them decompress.

• Encourage vacation time—some engineers won’t take breaks unless you tell them to.

• Respect their off-hours—if they’re in flow late at night, fine. But don’t make that the norm.

Some of the best ideas come when people aren’t working. The CTOs who get this right keep their teams going for the long run.

Kill the Bureaucracy for Them

Bureaucracy is where great engineering talent goes to die.

The best engineers want to solve problems, build great systems, and ship impactful work—not waste hours in meetings, fill out forms, or wait for approvals that shouldn’t exist in the first place.

The best CTOs act as a shield between their top engineers and the corporate sludge that slows everything down.

They don’t let engineers get dragged into pointless status updates, excessive process discussions, or convoluted approval chains.

This doesn’t mean throwing out structure entirely—some process is necessary to keep a team going in the right direction—but it does mean being ruthless about eliminating anything that doesn’t add real value.

If an engineer feels like they have to fight through layers of red tape just to get real work done, they’ll eventually decide it’s not worth the effort and move on.

Run A-Typical Team-Building Activities

Let’s be clear, most company team-building exercises suck.

More often than not you’re sitting around a Zoom call talking about what your favorite bird 🐤 is or something equally vapid.

Top engineers very much loathe these activities.

Here’s what good team-building for top engineers actually looks like:

• Go to a tech conference and talk about what you learned afterwards

• Get together a group of engineers and have one of them demo something cool she built

• Figure out a common non-tech interest & go do that without talking any shop at all

Typical, cheesy and lame team-building on Zoom (or even in person) doesn’t work with top engineers at all.

It will have zero impact and in fact can even have a slightly negative impact.

Give them Hard Projects, Discomfort is Good

Top engineers hate being bored.

If their work is too easy or repetitive, they’ll disengage and start looking for something more stimulating.

The best CTOs know that keeping them engaged means pushing them just beyond their comfort zone—giving them problems that aren’t easily solved, challenges that force them into new creative areas, and projects that stretch their thinking.

This doesn’t mean throwing them into chaos or overwhelming them with impossible deadlines, but it does mean making sure they are never coasting.

If they feel like they’re solving the same problems over and over, they’ll get restless.

The trick is to keep them in that sweet spot where the work is hard enough to be interesting, but not so frustrating that they burn out.

When engineers feel like they’re growing and tackling meaningful work, they stick around. When they feel stagnant, they start entertaining recruiter emails.

Don’t Force Deep Career Talk

The best technical talent does NOT love the quarterly, long lunch with their boss to figure out what their career goals & aspirations are.

In fact, a lot of top tech talent hates these conversations.

For the most part they appreciate the “light touch” approach to their career. They want a boss to understand them, but not get in too deep with what their next 5 years look like.

And they like a free lunch just as much as the next person, but not in a “give me psychological career support” kind of way.

They want things laid back and generally kept at a high level because they’re smart and they know what they’re doing already.

The rule of thumb is to talk about career aspirations about once a year. And don’t do it over lunch or something informal, have the discussion in the office where things feel more serious.

Listen Well

It may not seem like it but top engineers want to talk. A LOT.

Therefore, as a CTO if you want to manage them effectively you’ve got to listen and listen well.

Top engineers may come to you to complain, discuss a technical challenge or a myriad of other topics they want to cover.

And they may want to cover it repeatedly. So don’t be surprised if you’re having to do the same conversation multiple times.

What you have to do is perfect the art of listening patiently. No matter how you feel about the problem you’ve got to let the engineers vent.

Like many people this has a magical cathartic impact on top engineers. After being allowed to say their piece they tend to de-stress quite a lot.

Not every CTO has the interest or ability to frequently just listen for long stretches. But if you can develop this skill you’ll be much better off.

Take Care of the Rest of the Business

Nothing is more frustrating for a top engineer than dealing with problems they didn’t create.

When sales over-promises, when marketing misrepresents a product, when customer support is overwhelmed—these failures inevitably become engineering problems.

Suddenly, the best tech talent is pulled away from real work to fix issues caused by bad business decisions.

Great CTOs make sure the rest of the company is running well (to the extent possible) so engineers don’t have to clean up the mess.

They push leadership to set realistic expectations, they ensure product roadmaps aren’t dictated by sales desperation, and they shield their teams from distractions that don’t contribute to progress.

Engineers want to build, not constantly firefight. If the rest of the business isn’t functioning, even the best engineering team won’t save you.

Closing Thoughts

Managing top engineers isn’t about drowning them in motivational speeches, or forcing them into awkward team-building exercises where everyone pretends to enjoy trust falls.

It’s about recognizing that they are highly intelligent, highly valuable, and highly allergic to nonsense.

If you create an environment where they can build, break things (strategically), and get paid what they’re worth without being suffocated by bureaucracy, they’ll do the best work of their careers.

If you don’t, they’ll ghost you faster than a flaky recruiter after you tell them your salary expectations.

The biggest mistake CTOs make is assuming that what worked for the general workforce will work for their A-players. It won’t.

Top technical talent doesn’t need constant check-ins about their five-year plan, nor do they want to sit through another meeting that could have been a Slack message.

They don’t quit because the office snacks weren’t organic or because the company didn’t adopt the latest trendy productivity framework.

They quit because the work got boring, the leadership got dumb, or the company got in their way.

Challenge them, respect them, and—above all—don’t waste their time.

Because if you do, someone else will be happy to offer them fewer meetings, bigger problems, and a bigger paycheck.