March 1, 2018. I won’t forget that date any time soon because it was the day I made my first major mistake as COO… and it had taken less than 6 hours in the role to happen.
“We can’t keep letting this happen. We just lost one of our largest customers to a completely avoidable situation. We fell down on the job in supporting this customer and in fixing the technical difficulties they were facing.
We’re losing too many big accounts lately and we can’t afford to keep doing it if we’re going to grow as a company. Let’s get it together and start taking it more seriously to serve the creators who pay us every month,” I concluded to the entire company.
Fifteen minutes prior, on a Thursday afternoon, I had posted to our company Slack: “All-team meeting in 15-minutes at this link… If you’re not on a customer call at that time, stop what you’re doing and join this call.”
That’s Not How We Do Things at ConvertKit
We never have meetings like this. That’s not how we do things at ConvertKit.
We don’t stress people out by randomly calling meetings. We don’t call people out for their mistakes in front of the whole company.
There were multiple problems at play here:
- It was my first day in the role, so this was bound to come across like a power play
- I had just arrived for the first time to my new (empty) apartment on the Upper East Side in New York where my wife and I were moving from Portland, Oregon; the move was leading to a lot of stress outside of work, so every little thing at work was triggering me in a way that wasn’t helpful to anyone
- This is not the most effective way to create change that lasts in an organization
- It’s not how I want to lead or be led; the kind of people who call random meetings to call out mistakes are the kind of people I actively avoid
How had I let myself fall into this trap of leadership?
I couldn’t fret on that for long because the biggest problem of all was right in front of me: regardless of my intentions, I had created a lack of trust. The team perceived that I didn’t trust them and they certainly didn’t have trust for me in my new role.
You might say I had done the opposite of what you want to do on your first day in a new role.
A Step by Step Process to Recover from a Mistake as a Leader
Once you’ve made a mistake, there’s no taking it back. What you do next matters more than anything. Your job is to fix what you’ve broken and then take steps to make sure you don’t make the same mistake again.
Here are the steps to recover from a mistake:
- Recognize the mistake
- Understand who the mistake impacted
- Seek those people out and listen to how the decision affected them
- Apologize for the impact of your mistake
- Set principles for how you want to lead going forward
- Get to the bottom of the original challenge and solve it
Step 1: Recognize the Mistake
Unfortunately, too many leaders refuse to acknowledge their mistakes. I get it — it’s embarrassing. We’re supposed to be the ones who “know what we’re doing.”
This idea of leaders needing to be perfect is part of the myth that holds leaders back.
You need to know this right now: every single leader makes mistakes. Every single leader makes big, stupid, embarrassing mistakes.
What differentiates the kinds of leaders people will follow faithfully is how they respond to failure and mistakes.
To start the process of recovery, cool down from the immediate aftermath of the mistake. Then use the strategic powers you use every day to analyze what went wrong.
Which actions did you take and which words did you use that you truly regret?
In my case, here were my mistakes:
- Calling a meeting hastily while I was still emotional (angry) with the situation
- Lacking complete context for what happened that led the customer to cancel their account
- Addressing the issue with the entire team instead of working personally with the individuals who could impact the systemic problem in the long-term
In the process of evaluating where you went wrong, you’ll also recognize the truth in the mistake.
In my case, the following were true:
- There was an ongoing problem with large customers canceling their accounts
- We had problems at the product level that were frustrating our biggest customers and the customer success team was doing everything they could to cover for gaps in the product
- Large customers wanted fast responses and, ideally, someone they knew personally to stay in touch with them – we were providing neither at the time
It wasn’t that we didn’t have problems that could and should be solved. It was that I responded emotionally instead of rationally. In the process, I created more problems and no solutions.
The first step in recovering is to understand what your actual mistakes have been. When you can assess this on your own, you’re on the right path. When you can’t, you’ll have to skip to the next step and do some investigating.
Step 2: Understand Who You’ve Impacted
When you make a mistake as a leader, there’s always someone watching. The people who are watching are always impacted by what they see from you.
The road to recovery from a mistake that involves people (almost all mistakes involve people in one way or another) starts with connection. Your job is to rebuild trust with the people with whom you’ve broken trust.
In my case, I had inherently called out two people in everything but name. They had handled this customer’s support tickets.
Because I communicated that I didn’t think we were providing the support he deserved, it came across like it was their fault. I would’ve received the message the same way were I in their shoes.
In reality, we had a systems problem, which was a problem of leadership.
Impacting two people would normally be manageable. But in this case, I had directly impacted two people IN FRONT OF every single person on the team who was working at the time.
In the process, I lost trust with every person on the call. This was especially true for those on the team who had not worked closely with me in the past and who were already nervous about how I would perform in my new role as COO.
I had some serious cleaning up to do.
When you make mistakes, you need to take an assessment of who you’ve hurt in the process. Who have you impacted directly? Who else have you impacted indirectly based on what they have observed from you?
If you’re not sure, then skip to the next step and start by speaking with the people who might have been impacted or who might know who was impacted.
Step 3: Listen
Up to this point, you’ve not really had to face up to your mistake. You might feel a guilty pit in your stomach, but you haven’t actually looked anyone in the eyes and seen the way you made them feel.
This is by far the hardest step in coming back from a mistake you’ve made. You have to be humble, ask good questions, listen to how you’ve impacted people, and then apologize genuinely for the mistakes you’ve made.
One of the most frustrating (for you) parts of this process is that people are not on your timeline. They may not be ready to open up to you right now about how you’ve made them feel. You may not feel ready to apologize at the end of a single conversation.
You have to be patient and take the time necessary to get things back on the right track. The fastest way to avoid this is not to make the same mistake twice (which we’ll get to in a bit). The next fastest way is to be patient and make amends where necessary.
My process starts with scheduling 1:1s with the people I’ve affected, starting with the person who was most negatively affected first.
In these conversations, I let them know ahead of time that I feel I’ve made a mistake and that I’d like to hear how it affected them.
Then, I use open-ended questions to try to truly understand their perspective:
- How are you? (We use a system we learned from Reboot called Red/Yellow/Green to understand how people are doing when we start meetings. This helps us understand each other’s moods and make adjustments to our tone and agenda accordingly.)
- Can you tell me about what you experienced when [situation]?
- How did you feel when [mistake you know you’ve made]? (Consider repeating this question for as many mistakes as affected this person)
- If you were in my shoes, what would you have done differently in that situation? OR In the future, if we face similar situations, what can I do differently for us to tackle the problem together?
- Who else do you think I affected negatively?
The right questions will help you get to the heart of the matter. You’ll know what you did, how it made them feel, and what they would like you to do differently. You’ll also likely learn that you affected more people through your mistake than you thought you did.
Step 4: Apologize
Now here’s the kicker in this stage of the process: you have to apologize genuinely.
There are two kinds of apologies you should make:
- Apologies for your actions
- Apologies for how your actions made the person feel
Your actions will be the mistakes you made. The way you made them feel will be the gap between your intent and your impact (unless, of course, you meant to hurt their feelings).
When you’ve made a mistake, you always owe an apology for the negative feelings as a result.
That apology should look like this: “I am sorry that I made you feel [feeling] when I [action]”
The apology should not look like this: “I’m sorry if you felt [feeling] when I [action].”
The first apology takes ownership for your mistake. The second apology is passive and does not take ownership of your mistake. If you’re not ready to apologize yet, then no apology is better than an apology that lacks ownership.
Consider working with a coach or mentor to get clear on your mistakes and what you should be apologizing for so that you can apologize genuinely.
When you’re ready, make your apologies and commit to avoiding the same mistake in the future.
Step 5: Set Principles to Avoid Similar Mistakes in the Future
There is one key difference between growing from your mistakes vs staying stuck in your negative habits at work.
The key: Don’t make the same mistake twice.
This is easier said than done, especially when our mistakes are a result of our weaknesses. They are likely to pop up over and over again in our career.
While we can work hard to minimize exposure of our weaknesses, we cannot avoid them altogether.
This is where principles come in. When you establish principles, you’ve made a decision once instead of making the same decision 100 times over.
Here are some example principles that have come out of the situation I opened this essay with (as well as other mistakes along the way):
- Don’t call unscheduled all-team meetings unless they are for fun, optional, and to celebrate (Exception: when information must be communicated quickly in order for it to be communicated well, such as when someone has decided to leave the company)
- When I am feeling strong negative emotions in a meeting, but am not sure why, say that out loud and take a step back from the conversation
- Critical feedback is best delivered 1:1
- Problems are better solved through systems than one-off bandaids
Setting your own principles can help you avoid making the same mistake twice. People will regain their trust when they see similar situations that result in different actions from you as their leader.
Step 6: Solve the Original Problem
Now that you’ve identified your mistake(s), understand who you’ve impacted, listened to how you’ve impacted them, apologized, and set principles to avoid making the same mistake twice…
Only now can you circle back to where this all began and solve the original problem. I find that most of my mistakes come in moments of stress, tension, or conflict. These are often the result of problems that do genuinely need to be solved.
Trust is the basis for any great solution. With trusting relationships, a group of people can come up with great solutions that will last over the long-term.
In our case, the problem that drove my big mistake was one that had deep roots. Over more than a year, we worked to hire many more customer support specialists so we could respond to customers faster.
Then, we added a new role to the company. Account managers now handle a portfolio of large customers and serve as the primary point of contact in the company.
Finally, we invested heavily in making our product more delightful to use so that our customers would have fewer frustrations to begin with.
As with any true solution, this has taken time. And that was my ultimate mistake: thinking I could solve a tough problem with a hard-nosed call on my first day on the job.
Now I know better.
No Leader is Perfect
Leaders make mistakes. We’re just like every one else in this regard.
What is different about leaders is that people look to us in times of stress and difficulty more than ever.
Acknowledging, apologizing for, and then correcting for your mistakes will make a positive impact on everyone on your team.
Next time you make a mistake you regret, consider following this process to make it right.