Mastering Damage Control: A Top 1% Skill (Part 2)
Part 2 of 2: How the Best Leaders Limit the Impact of Their Failures
Hi Technocrats,
Like me you’ve probably added several pounds of Turkey 🦃 weight recently.
But now it’s time to turn yourself into a bada** again.
This time by mastering the art of damage control and turning your epic fails into epic wins. 🏆
Let’s do it!
Cheers,
In Part I of our discussion on this topic we talked about how top leaders are masters of damage control.
We also covered the typical failure modes & self-inflicted wounds of leaders who are trying to rise to the top.
Here’s the list of typical failure modes of ambitious, top leaders:
Failure Mode 1: Lack of Patience
Failure Mode 2: Pretending You Know Everything
Failure Mode 3: Too Many Masks & Insecurities
Failure Mode 4: Lack of Tolerance for Mistakes
Failure Mode 5: Too Many Preconceived Ideas
Failure Mode 6: Too Easily Hurt / Thin Skinned
Failure Mode 7: Not Enough Focus
Failure Mode 8: Not Staying in Their Lane
Failure Mode 9: Assuming Political Capital is Infinite
Failure Mode 10: Too Big of an Ego
If you want more details go check out Part 1: https://newsletter.technocratic.io/p/mastering-damage-control-a-top-1
Now it’s on to Part 2: tips for running damage control when things are falling apart.
Caveat
A lot of people will say damage control is about avoiding responsibility for problems.
And, that leaders should instead focus on learning from mistakes & improving themselves instead of spinning the story.
My take is that good leaders need to do both damage control and take responsibility for their failures — its not mutually exclusive.
And damage control is not about looking for a way to absolve yourself of blame; it’s about identifying opportunities in the midst of problems.
It’s he best form of taking ownership because it’s taking ownership with actions to improve.
With that in mind let’s jump into successful damage control strategies.
Damage Control Strategies
Have you noticed how some execs will make huge mistakes but still somehow come out unscathed?
It’s not just luck or charisma — its the art of damage control and they’re very good at it.
Failure is inevitable in leadership. Decisions are made with imperfect information, risks don’t always pay off, and sometimes, things just go wrong.
But managing the actual impact of failure is where the real art is.
These are 7 strategies that I’ve seen used effectively — let’s dig in.
Strategy 1: Predicting Your Own Failure
Really good tech leaders know how to anticipate when things are going to go wrong. They really don’t need others to tell them if their own project is going to fail.
They know it well in advance & they plan for how to handle an unfortunate situation.
In fact, they will typically do a lot of risk planning before the project even begins. Far, far more than most average leaders realize.
Thinking through potential future ways a project is going to fail is a very powerful tool. And it isn’t seen as anything negative amongst top performers.
It actually builds a kind of immunity in them so that no matter what happens top leaders are ready for it & not worried or overly stressed.
And it’s really not that complicated, either.
There are really less than 10 ways most tech projects or initiative can fail. So doing the work of thinking through failure modes and what to do about them isn’t that hard.
If you do this at the start of a project you’ll thank yourself later if anything goes wrong. It’s just a kind of insurance policy for smart leaders.
Strategy 2: Designing Multiple Backup Options
This connects to strategy #1.
When you think of a future where perhaps your project fails what would the “fall back” or secondary set of backup options be that you could pivot to?
Pivoting is an excellent form of damage control.
It’s taking what you have built (which perhaps is good but didn’t work perfectly for whatever reason) and either repurposing it or changing your strategy altogether.
Preparing for a potential pivot is a wise investment to make.
Think of it as a contingency plan — especially for high-risk initiatives.
The reason pivots are used by top leaders is because if done right it gives minimal time for stakeholders to sit and dwell on any failures.
Instead the failing effort is framed as vital learning (but only if it actually is, don’t make anything up) for the new / next / backup option.
Strategy 3: Line Up Your Allies
In life we usually need others to help us succeed & this is true in companies as well. You are usually not going to win alone — you’ll need allies.
And these same allies will be needed if a project goes south on you and you need help.
You must build coalitions of support before problems occur. These stakeholders must be the type that can help support your recovery from a miss.
Keep your allies regularly updated about risks and challenges.
This means it’s vital as a top leader to build strong relationships cross-functionally in the organization.
This is a big part of damage control and risk mitigation. If you have strong relationships it can save you.
Know who has your back in a crisis and lean on them strategically. And acknowledge and return the favor when your allies help you.
Strategy 4: Identify Challenging Parties & Their Arguments
A really good friend and fellow CTO of a world renown company once said to me, “you’re not doing well if you have no enemies.”
Kind of funny but also kind of true.
You must understand who will be your biggest detractors if you fail.
These may be perfectly great people but they may have their own competing set of priorities or personal biases.
The key is to understand at all times who will oppose you and why.
You don’t have to write anything down but think through what arguments these parties will make related to your potential failure & how to address them.
In fact, you should anticipate what worst-case narratives your critics might spread.
Of course the ultimate way to handle challenging opponents is to find ways to align their goals with yours to neutralize opposition.
So engage detractors early & understand them well.
Strategy 5: Stay Calm
With average leaders when failure is looming in front of them they tend to over-react to the situation.
I know it’s hard to handle a situation when it’s not going well, but to be a top leader that’s exactly what you have to do.
Your composure sets the tone for everyone else including important stakeholders.
Don’t get me wrong though, I’m not suggesting being aloof to failure.
Simply avoid visible panic; it erodes confidence among your team and stakeholders. And pause before reacting to give yourself time to think rationally.
Focus on actionable steps instead of dwelling on the magnitude of the problem. Communicate calmly and clearly, even under pressure.
Set a measured pace for resolving the crisis, avoiding knee-jerk solutions.
And, remind your team that almost every setback is only temporary and probably solvable.
Strategy 6: Write a Narrative that Transforms Failure into Opportunity
At some point if you’re running a project that fails, you’re going to end up building and presenting a deck with what went wrong and how you’re going to fix it.
On that day your narrative game better be on point.
You’re going to have to tell a pretty compelling story about how you’re going to fix things and get everything back on track.
It will have to be a forward-looking story, but still acknowledge past failures. And it’ll have to inspire confidence in others. They will need to believe you.
Doing that is challenging even in the best of times.
Here’s what top leaders do: they practice telling stories and designing narratives until they are really good at the art of it.
If you’re not good at this then take time to learn this skill because it’s vital for damage control.
If you can’t tell compelling stories then stakeholders won’t be as willing to follow you, especially after a big miss. So pay attention to this one.
Strategy 7: Rebuild Trust with Stakeholders
Damage control isn’t complete until trust is restored.
A lot of CTOs ask me how to do that.
The answer is painfully obvious: generate results.
It’s not about going hat-in-hand to say sorry. No one cares.
What they care about is results.
Follow up with key stakeholders to show them the positive outcomes you’re creating after a bad miss.
Be honest about what went wrong but show them how the right things are starting to happen.
Share specific actions you’ve taken to ensure the results WILL KEEP COMING.
Solicit feedback from stakeholders to demonstrate openness. But its most important to simply show progress and new momentum after the crisis.
Bonus Strategy: Assume 10% Will Fail
When was the last time you lead or observed a project meeting 100% of its goals?
Most aggressive and worthwhile projects do not meet 100% of their goals - that is simple statistics.
Therefore, ask yourself what 10% of your project is going to fail and then prepare accordingly.
Top leaders ALWAYS know some part of their effort is not going to work out right, and they get busy figuring out what part that is likely to be.
Once they determine that they think through mitigation steps & contingency plans.
Closing Thoughts
To the best leaders damage control is not a bad word, its simply a skill they have to perfect over time.
These leaders are doing difficult things, that’s why they are in the top 1%. And if you’re doing difficult things you’re going to encounter failure. That’s just life.
The best leaders simply have the best reactions to failure. They know how to take a disaster and turn it into a win for the company.
And not in some fake or made up kind of way but in a real value-generating kind of way. A way that’s thought-through. A way that shows they’ve done their homework.
The art and skill of damage control lies not in avoiding responsibility but in embracing it in a highly prepared manner.
By preparing for all positive and negative eventualities top leaders are able to turn failure into success much more frequently than average leaders.
Leaders who master this skill gain respect and credibility, even in challenging times.
As a CTO, your ability to manage failure doesn’t just protect your reputation — it protects your team too.
So start turning setbacks into stepping stones.
And in the meantime, if you need anything feel free to email me at bobby@technocratic.io