How to become an “Undercover Boss” Superstar

Does this really fool people??

I’m a firm believer in having a team that will be 100% honest with me. I want unvarnished, unfiltered information and opinions about the issues of the day. That way, as a leadership team, we can make the best decisions to deal with real issues. If my team is trying to show me an overly rosy picture, I can get a false sense of security about how things are going. Trust and openness are essential for high-performing teams. I think I do a good job at creating those environments, but still, despite that, my teams will sometimes fall into the trap of downplaying issues and avoiding those real, and sometimes tough conflicts. It’s human nature.

So it is essential as a leader to check in different ways if what you’re hearing and seeing is real. It’s not a lack of trust, but a check on whether your team is falling into a trap of hypnotizing each other to believe something that isn’t real.

Let’s face it, the pace of work is faster than ever before, and it’s so easy to let all the details go and focus on the bigger picture. The big picture is important for sure, but success happens in the weeds, not in the sky. If you don’t have complete alignment from all levels in your organization you are doomed to fail.

Hearing what others in your organization really think of things can also be incredibly humbling. I’ve been wrapped up sometimes in my own self-congratulation for deploying something bold and creative and inspiring, only to be dealt a cold splash of reality when someone tells me my idea won’t work. Or sounds stupid. Or doesn’t connect with them. It hurts the ego but getting our egos deflated a little can be very healthy and therapeutic and make you a much more human and engaging leader.

And you don’t need to go undercover to get the truth.

How to Know What’s Really Going On

So how do you know what’s really happening? There are so many great tools to get instant feedback from a large team quickly, and automatically. More than that, though, some very low-tech ideas work great too, and I am a big fan of real face-to-face honest discussions.

  1. Walk the Floor
    • It sounds really basic, but when’s the last time you walked around, said hi to people, and stopped to listen to how they’re doing? We all get busy, and sometimes it’s simple to rationalize that you will go see people later, talk to them when it’s quiet. But it’s an excuse to avoid hearing what is happening, and let’s face it, it’s never quiet. Get off your ass, and go say hi.
  2. Skip Level discussions
    • A skip-level meeting is one where you randomly pick some employees of your managers to ‘skip a level’ in the hierarchy and meet them in an open-forum setting to hear what’s happening. There are already a lot of good blogs and websites to help with structure and content so I won’t focus on that here. This is a good one for some good leading questions to ask. It’s really important to keep your manager that you’re “skipping” in the loop so it doesn’t destroy trust with them.
  3. The 5a7
    • Ah, the after-work ‘forced’ socialization. For those of you not in Quebec, the “cinq a sept” is a drink after work somewhere. I’m mixed about how I feel about these events. On one hand, they can be an excellent source of unfiltered truth and an informal, less stressful place for employees to open up. On the other hand, it can put pressure on people to show up to fit in, be seen, or interact with people they may not want to. Or if you aren’t a drinker, then it may not be your kind of event but then you could feel left out opting not to attend. Either way, if you do have these types of get-togethers, keep your ears open for honest feedback.
  4. Officevibe and such
    • I got introduced to Officevibe recently, and it is a fantastic tool. It’s free to use for basic services, but still provides a lot of meat without having to pay for premium. Signing up your team is as simple as pasting their email addresses, and can even be done automatically if you’re using slack or other tools like that. Once active, it will send out 2-minute surveys to everyone and you will get instant results on how your team is feeling and the biggest issues they have. They can leave anonymous messages for you too and you can reply to them to tell them what you’re doing with their feedback. You can also publish and share KPIs and trends with your team to show how the vibe in the team is improving.
  5. Engagement surveys
    • Like officevibe, these will give you anonymous insights as to how your team really feels. They are more structured tools: longer to complete, usually administered by an outside firm to ensure anonymity, and with a more scientific approach to analyzing the feedback. They can take a long time though, so use this if you have a very large team, and are looking for bigger issues.
  6. Go and See
    • In the language of Lean Manufacturing the “go-and-see” is simply that: when you are in a meeting with your team, and they bring an issue to your attention, get up and go see the problem first hand. Sounds obvious right? It’s surprising to see when I was learning Lean for the first time how little we did this before. We hear every day about things happening on the production floor, accounting, engineering, and discussing solutions in a meeting room. Why not bring the meeting to the problem so you can get a real feel for it? Not only that, you engage with the people living with the problem, hearing them out, and engaging them in the solution. And they get to see that you actually give a shit about them. Win-win.
  7. All Hands reviews
    • Depending on how big your team is, this can get really challenging. I remember being in a team of 3000 when the leader had an all-hands in an airplane hangar; it was like a rock concert (though way less exciting). But it is so invigorating when you get to talk to everyone all at once. Everyone hears the same message and you get to deliver it your way, without the broken telephone game of cascading a message down your organization. It’s also a place where you can practice being vulnerable and acknowledge the hard feedback you may have heard from the above options and show that you care about it and list the actions you are taking or have taken. People don’t often speak up, especially in large groups, but there is usually one brave soul who steps up and challenges you. Make sure you thank them, and no matter what, always tell them it is a great question and answer it honestly. Everyone is watching you, so to encourage that openness, be completely open with whatever answer you give. How you act at that moment is your personal brand of leadership, so take it seriously.

Thank you sir may I have another?

Feedback is a gift. Sometimes the gift is like a fine bottle of wine. Sometimes it’s dog-shit in a brown paper bag. But it’s always a gift. Be thankful for every honest piece of feedback you get. Show your gratitude to everyone you interact with. This will breed a culture of honesty and transparency that is essential to every healthy organization.

Resist the temptation to correct, debate, or defend against particularly uncomfortable feedback. You can squash motivation in an instant by doing any of these things. Welcome the feedback, thank them for their courage in speaking up, and promise to get back to them on it. Just by doing that, you are building transparency, honesty, and engagement with your team.

Hearing the honest truth can sometimes bruise your ego, or even crush it altogether. But what’s better: knowing people are unhappy and that your team needs work, or thinking you’re awesome while people bitch about how out-of-touch and useless you are, then decide to leave?

I’m listening, now what do I do?

So now you know. As GI Joe would say, “Knowing is half the battle”. The other half of the battle is what you do with it. All the talking and listening in the world won’t fix anything if you don’t take it seriously and do something about it. Depending on how you gathered information and what you learned, your actions may take different forms. But prioritize them, make them your own strategic objectives and deal with them promptly.

If you have focus groups, skip-levels, or informal chats, it is absolutely essential that you follow up with the people with whom you interacted, and let them know that you are doing something about their thoughts.

If you collect survey data, share it openly, ask for comments, and build an action plan with a team of engaged people.

Then, don’t stop. If you want to have a company that people want to join, stay and thrive in, you make this a continuous process. Treat people like equals, like humans, and they will reward you with loyalty and passion.

The trust gap

I have one final thought about this topic, and I think it is more important than everything else here. Your team will look at you with skepticism when you are doing any of the techniques described here.

It is and will be hard for them to open up completely. You’re the pointy-haired boss, the guy who can hire and fire. Some people will never trust management; maybe because of past bosses, or other personal issues.

You have to work extra hard to earn their trust to share the unvarnished truth. And you can lose that trust really fast, if you never show them that their feedback leads to real change.

The most important thing in all of this is to make sure you take care of anyone who dares to be bold and shares with you their real problems. Give them your answer, your plan, your gratitude. That’s the hard work, and rewarding life of being a leader.

Author avatar
Sean Johnson