Mastering Damage Control: A Top 1% Skill (Part 1)
Part 1 of 2: How the Best Leaders Limit the Impact of Their Failures
Hi Technocrats,
“Failure is not an option.”
This is a popular line from the movie Apollo 13, which tells the story of NASA working to bring home 3 astronauts after their spacecraft suffers a major malfunction.
It’s a cool line, but in life failure is indeed an inevitable part of our journey, including those of the top 1% of CTOs, CPOs and CISOs.
The question is how you manage through it as a leader and run damage control effectively. This is what the top 1% of leaders seem to great right.
Let’s get into it!
Cheers,
Even the best of us fail at times.
It doesn’t matter how many years of experience we have or how knowledgeable we are, failure is a normal part of anyone’s tech career.
This goes for high-achieving CTOs, CPOs and CISOs at the top of their game, as well.
If you’re still climbing the corporate ladder don’t assume that people in these higher executive positions don’t have big misses & complex challenges to face — they do.
The more important thing to consider is not to avoid failing but to limit the impact of your failures on yourself & the environment around you (your company, your team, etc).
The top 1% of tech leaders are masterful at damage control. And if you can learn this skill too, you’ll go much higher and farther.
So, forget avoiding failure, and instead learn how to prevent it from really blowing things up.
Why Top Leaders Fail
Before we get into damage control strategies it’s really important to understand why leaders fail in the first place.
If you know the common “failure modes” then you’ll be able to handle damage control more appropriately when your time comes.
And your time WILL come — remember, every leader fails at some point in their tech career. It’s just a questions of when and how bad the impact is.
Caveat
When we talk about failure modes we won’t be covering tactical level problems.
For example, we’ll skip talking about these kinds of issues:
Built the wrong product
Deleted the production database
Missed a major release date
Yelled at the boss
Fired the only person who knew where the company bitcoin wallet password was stored
Hired a crazy person
These scenarios all suck, to be sure, and I truly feel bad for anyone going through them. But we’ll be diving into more strategic-level missteps.
Many of the failure modes we’ll explore will be self-inflicted wounds, i.e. challenges top leaders create for ourselves for one reason or another.
Let’s dive into them.
Failure Mode 1: Lack of Patience
When you’re earlier in your career your sense of urgency, assertiveness, and even lack of patience is actually an advantage: you get things done faster than your peers.
However, the higher up you go on the career ladder the more patience & thoughtfulness you need to have to succeed.
This is initially counterintuitive because most of us assume that with more power comes the ability to quickly execute on whatever we wish.
But the reality is that commanding larger teams on more meaningful projects actually involves taking more careful & methodical steps.
Top leaders will sometimes forget this and act almost recklessly at times.
For example, I’ve seen many good leaders undertake poorly conceived of projects rife with issues, that ultimately failed just because they didn’t have the patience to do their due diligence before starting.
So impatience then can very often trip up top leaders.
Failure Mode 2: Pretending You Know Everything
I once had a boss (CEO) that admitted she didn’t know everything.
It was a refreshing approach since most execs tend to project the aura that they have the answer to every problem. It made everyone like and respect her more. And we were willing to go the extra mile for her.
Pretending you know everything is a common phenomenon amongst top leaders which very few are able to avoid. When a person is put in charge, even if they are naturally humble, there is a natural pressure to always be right and know everything.
Don’t fall into this trap because it can really hurt your leadership.
For example, pretending you know everything can create scenarios where you lead a team towards the wrong goals or direct them using the wrong strategies.
High-achievers can sometimes find it very difficult to admit to any knowledge or skill-gaps which can lead them to failing at capitalizing on big opportunities.
So avoid this failure mode at all costs although it’s difficult to do so for even the best leaders.
Failure Mode 3: Too Many Masks
We all know the concept of highly successful but equally insecure leaders. In fact, we see these personalities in leadership everywhere around us.
The more insecure these leaders are the more they tend to wear different masks to cover up their self-perceived weakness and flaws.
This in turn makes them less authentic & harder for their teams to bond to and follow into battle; mainly because they don’t know who the leader really is underneath.
It’s better to avoid too many masks or you risk coming across as too much of a manipulator even though you might not be.
This in turn can create a lower quality culture that effects the performance of your team & organization.
Of course, as humans we can’t help wearing at least some masks, but being relatively authentic is always a good thing for your leadership.
Failure Mode 4: Lack of Tolerance for Mistakes
Top leaders often have a penetrating ability to spot the mistakes of those around them.
They are so good at what they do, and have mastered their domain so well, that their sensitivity to any errors is extremely high.
But Marcus Aurelius (the famous Roman emperor) reminds us to “be hard on ourselves and easy on others.”
Pointing out other peoples faults is easy for top leaders, but it creates an atmosphere of distrust & dislike. It’s far better to quickly fire the person if they aren’t performing and save everyone the grief & tension.
As a leader, if you lack the tolerance for mistakes it makes you too rigid and inflexible.
It’s actually through mistakes that a lot of breakthroughs can be created. But if you don’t have the tolerance you create a static, almost frozen culture that limits innovation.
I’m not saying tolerate lots of mistakes all the time. But not having any appetite for acceptance of misses is a common flaw amongst leaders and it really hurts them in the long run.
Failure Mode 5: Too Many Preconceived Ideas
Hyper-successful people can often have a lot of preconceived notions about industries, markets, companies, how to run departments and so forth.
When some leaders get very successful on one thing they start formulating ideas about other things thinking they’re smart enough to grasp it all.
Don’t be this kind of leader.
You don’t want to get successful and then stop learning from others because you think you know it all.
But a lot of execs fall into this failure mode: they run around with preconceived ideas and don’t realize they are making mistakes because of them.
Even the best CTO or CPO or CISO still has INFINITE room to learn — about industries, companies, customers, etc, etc.
Failure Mode 6: Too Easily Hurt
I used to be pretty thin-skinned early in my work journey and I’ve met a lot of tech leaders who remain that way throughout their careers.
Sure, there’s nothing wrong with being sensitive, but in our industry there is a lot of crap that top leaders have to take from all directions.
It’s just part of the job.
Being too easily hurt by criticism can lead you to failure mainly because you start acting emotionally instead of with clear, rational thinking.
It can also cause leaders to make certain decisions they wouldn’t normally have just because they were criticized — don’t do this!
Being really thin-skinned doesn’t make for a strong leader. Your teams can see it and it encourages them to lose confidence in you.
Failure Mode 7: Not Enough Focus
Top leaders who are good at many things often have a multitude of priorities, and with that comes the potential to spread themselves too thin. However, lack of focus can lead to critical failures.
When you try to tackle too many things at once, you risk diluting your impact and missing the mark on what truly matters.
Successful leaders know how to identify the most important priorities and ruthlessly focus on them, even if it means saying no to other seemingly good opportunities.
Failing to concentrate your energy on a few high-impact initiatives often results in stalled progress, frustrated teams, and wasted resources.
Remember, focus isn’t about doing less — it’s about doing what matters most — which is high ROI business activities.
Failure Mode 8: Not Staying in Their Lane
As a leader, you’re expected to have a broad understanding of your organization, but that doesn’t mean you should meddle in every area.
One common failure mode is overstepping your bounds and getting involved in areas where you lack expertise or aren’t needed.
This often stems from good intentions, such as wanting to help to ensure success. However, it can undermine others & take their initiatives down the wrong path.
Great leaders trust others to do their work.
If you’re awesome at Product and Technology be careful about thinking you can “fix” Finance, HR or anything else. You may not realize many of the nuances in those areas.
Tech leaders can fail if they stray out of their lane too frequently and without thinking it through. If you’re asked for help then help. But don’t take things too far.
Failure Mode 9: Assuming Political Capital is Infinite
Political capital is like any other resource — it’s finite and needs to be managed wisely.
Leaders often fail when they assume they can keep cashing in on goodwill, influence, or authority without replenishing it.
Whether it’s pushing for one too many ambitious projects, asking for additional budget without delivering results, or leaning on your relationships without giving back, overuse of political capital can quickly erode your standing.
The best leaders carefully build and conserve their political capital. They know when to spend it and when to hold back, ensuring they always have enough in reserve for when it truly counts.
The only person who had infinite political capital was probably Steve Jobs at Apple. But then Steve was a genius who was constantly hitting home runs.
Failure Mode 10: Too Big of an Ego
I saved the best for last. This is the most common failure mode in my view.
A healthy level of confidence is necessary for leadership, but an overinflated ego can be your downfall.
Leaders with outsized egos often make decisions that prioritize their own self-interests over the organization’s best interests.
They might dismiss feedback, ignore red flags, or refuse to admit mistakes because doing so would challenge their self-perception.
This creates blind spots, alienates teams, and ultimately leads to poor outcomes.
The best leaders stay humble, no matter how high they climb.
They recognize that leadership isn’t about feeding their ego but about serving the business and delivering results.
Low-ego leaders just win more.
I actually don’t even think its low-ego as much as it is their ability to control their ego when it really matters.
Too many executives lack this.
Conclusion
Running damage control effectively is a vital skill to master in order to be a top 1% tech leader.
Today we walked through the various strategic-level “failure modes” for execs trying to break into the top ranks.
Now that we’re clear on what some of these are we’ll tackle specific damage control strategies in Part 2 of this article.
If you’re trying to crack into the top 1% just remember one thing: some of it is reducing the amount of failures, but it’s more important to limit the damage of those failures.
Misses will happen in your career but you need to know what to do with them.
OK, so I’ll see you in Part 2 where we’ll dive deep into damage control strategies.
And in the meantime, if you need anything feel free to email me at bobby@technocratic.io