What Are You Optimizing For?

How often do you catch yourself in the middle of some fight only to realize it doesn’t really matter? Or, how many of your opinions are “strongly held” even though they’re no longer serving you (if they ever have)? A prevalent leadership fallacy I come across is seeing clients who are optimizing the wrong metric.

The problem, unsurprisingly, is that this failure to articulate the right measure means leaders are unlikely to be successful—at least not as successful as they could’ve been. Some of these are head-smackingly obvious to any external observer (is “facepalmingly obvious” a thing?), whereas others could require a lot of work to uncover and express eloquently. To help you tease out areas in your organization that would benefit from tuning or a fresh perspective, I will list some typical scenarios I’ve helped clients overcome.

As you’ll see, this problem can occur at any aspect of leadership, including management basics, strategic orientation, and technical alignment.

People Being Happy

Clearly, no one is going to claim they’re optimizing to make their people unhappy! Nevertheless, putting too much stress on that can put things out of whack. After all, no matter how many times you’ll repeat it, your company is not a family. People cannot leave a family or be forced out of them.

That’s not the case for companies where an employee might decide to leave for a myriad of reasons or when an employee has to be let go. Similarly, I’ve seen executives boasting the fact that no one has quit their teams in years, or ever! This is similar to the “happy people” metric, and the issue with both is it can lead to racking up lots of organizational debt.

When your goal is to keep people around or happy at almost any cost, you stop doing what’s best for your organization as a whole. That frequently leads to convoluted org-charts, slow-to-move teams, and a union-like atmosphere that invites politics and ongoing bickering. It’s counterintuitive that a focus can result in this, but that’s the result of anything taken to an extreme.

Never Firing Anybody

The other side of the coin for employee happiness is resolving never to fire anyone. At some companies, this means that an existing manager, even after over a year of active coaching and mentoring, can still be underperforming and not be let go (or moved back to an IC role). Others focus more on the hiring part and want to ensure that they never hire anyone just to realize two months later a mistake was made.

The former means that we are doing the rest of the team a disservice and, frankly, to the underperforming employee as well. I wholeheartedly believe that in cases with a clear mismatch, after investing our time and attention, it might be time to cut our losses short. Just because someone wasn’t right for this specific job, in this specific team, right now, doesn’t mean they’ll never be able to do it properly. But rather than keep on trying to shove square pegs in round holes, you should help them find something else for the time being and try again at a different time.

When it comes to the latter, an organization that does not allow itself to make mistakes when hiring is not likely to be able to grow fast and will miss out on a lot of great talent. Those constraints might fit your company like they do Google. But, for the vast majority of startups, I believe that aiming to have an 80% success rate is better than aiming for perfection.


Even when we have the best intentions in mind, the wrong focus can lead us astray. Such is the case when we emphasize rote delivery without considering what it is achieving. I see teams that meticulously track velocity, sprint completion rates, and delivery speed. These metrics have their place and can provide valuable insights, but when they become the ends and not the means, we lose sight of what we are trying to achieve.

Tracking output doesn’t mean that we’re getting the right outcomes. Doing things right is less valuable than doing the right things. Help your team achieve real impact by making them gaze up from the keyboard and realize their efforts’ results. For example, hold meta-reviews (as covered in The Tech Executive Operating System) to retrospect not just how the work was accomplished, but what has it actually achieved. If a feature is deployed and no one uses it, does it make a sound?

Tech for Tech’s Sake

Similar to the last point, sometimes, as part of our search for meaning and self-actualization, we find the path of least resistance. When the company is not good at connecting the R&D team to the business, the engineers find another outlet, which is often the technology itself. That’s why you can often find tiny startups with CI/CD setups more appropriate to public companies or companies that are failing to get any talented engineers because a handful insisted on using an obscure language no one else knows.

Yes, creating software is a craft, and we should strive to be great at it, but that’s not what we’re getting paid for. No CEO woke up and decided to allocate 30% of her budget for some nicely space-formatted, SOLID code. What she is after and what the team should be after are results.

Cost vs ROI

One last example is another one of those obvious-after-you-point-it-out cases. When companies strive to lower costs, as opposed to considering the value that they are getting from something, they are bound to get what they pay for. Not paying top talent market rates? You’re less likely to get high-caliber hires. Outsourcing work to save on costs? That’s definitely not going to achieve the same results as outsourcing based on ROI.

I have family members that are like this in their day-to-day. They’d buy a bucket of tasteless strawberries because they were cheap somewhere. When they see me get a small box that costs more at a farmers market, they cringe. For them, it’s the cost; for me, if I’m eating a strawberry, I want it to taste good. You cannot use watery strawberries to make a fantastic dish.