As an executive onboarding into a new role, you don’t know what you don’t know. That’s often an underlying factor when people don’t fit, fail to deliver, or fail to adjust to changes down the road. If they’d only known the problem, they might have dealt with it. Build a network of external scouts and internal seconds and spies to help you understand what you’re getting into.


Scouts are external people with different perspectives. They could be customers, suppliers, allies, competitors, part of the community, regulators, analysts, journalists, former employees or anyone looking at the organization from outside.

These people are relatively easy to identify if you put in the effort and generally are willing to share what they know. Note they are – by definition – external and can tell you only what they see. They won’t understand the underlying drivers of the organization’s decisions and ways of working.

Leverage scouts to help you prepare for interviews, do due diligence, prepare for Day One and throughout your tenure to help you see things you might not see. Often outsiders see things that insiders don’t. Scouts can help you see changes down the road so you can adjust as appropriate.


Webster says a second is “2 one that assists or supports another especially the assistant of a duelist or boxer.”

It doesn’t matter if these people are your boss, peer, subordinate, mentor or onboarding buddy. These are internal people that are explicitly assisting or supporting you.

These people can ask questions that you may feel uncomfortable asking yourself. Some people will tell these people things that they don’t feel comfortable telling you directly, knowing the second will filter what they said and pass it on – sometimes with attribution and sometimes without. In any case, part of assisting or supporting is creating another channel of communication.

Leverage seconds both proactively and reactively. The ABC’s of behavioral influence apply. ABC stands for Antecedent, Behavior, Consequence. People do things because an antecedent prompts that behavior. They do it again because of the balance of consequences: rewarding or punishing desirable or undesirable behavior.

So, if you want your seconds to identify things that could be going better, proactively prompt that behavior by explicitly asking them to do so. Don’t expect them to do it on their own.

In any case, when one of your seconds comes to you with bad news, make sure you reactively respond in a way that encourages them to do it again. Not only should you not kill the messenger of bad news, you should reward them.


Spies are internal people who observe what is going on and tell you about it. Every organization has hidden back channels of information flows. I’m not suggesting anything hostile or inappropriate. I’m just suggesting that you make sure you’re in the flow of at least some of those back channels.

If your new organization uses executive assistants, they form a natural back channel. Make sure your executive assistant is in that flow and shares things with you. In this case, your executive assistant is both a second and a spy.

One of my personal favorite ways of creating spies is to go three levels deep. After year-end-reviews are completed, get a list of your subordinates’ subordinates’ subordinates who got the top-box performance rating. Then arrange to have a one-on-one lunch with one of them each week for as long as it takes to get through all of them.

Read their review before lunch and say “I’ve read your review. You’re doing great things. I asked you to lunch to learn more about what you do.” Then listen.

It’s a great way to recognize strong performers. They will feel better about themselves. It’s a great way to learn about what your strong performers are doing and how things work.

And, it’s a great way to build your spy network. After this lunch, these people will know you better. They will tell you what’s going on. Your subordinates have a bias to tell you what they think you want to know. Their subordinates don’t want to get their bosses in trouble with you. But those three-levels deep are too far away to be afraid of you. They’ll tell you the truth.