THE LEAFLET

April 03 2025

why new leaders avoid goals, mistakes to avoid in stakes-y meetings, in the game for the right reasons

WHY NEW LEADERS AVOID MAKING GOALS

New leaders often show a reluctance to set bold goals for their teams. Among other things, a goal is a bet on the future, and these leaders feel bad making such a bet.  

It’s possible these leaders feel better trusting their perspective and read of current context than to boldly state what they want their team to make true weeks or months in the future. Epistemically, they have more confidence in real-time problem solving.

At the most basic level, though, the allergy to setting goals can be drawn to something that runs under all early leadership: fear of the power that I'm actually responsible for wielding at this moment. Someone new to leadership may say, “It doesn't even feel right to make a bet on this.” What they're actually saying is something more like, 

“What I've done before this is work for people who are making bets like this in ways I didn't understand. I’ve done work that feels experientially valid and leads to some good outcomes. But I have not yet been responsible. I have not yet associated my performance, my sense of being good at work, with having to set a pretty bold goal and work towards it. Up to now, my leaders have been doing that part for me. Nobody told me that's what I'm going to have to do now that I’m a leader.” 

-ben

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MISTAKES TO AVOID IN STAKES-Y MEETINGS

If you’re taking Cate Hall’s wise counsel and being more agentic, you might land a meeting with someone whose help / support / resources you want. They’re a donor or connector or prospective boss. Or maybe they’re a senior peer - someone similarly situated but further down the road you’re walking. They’ve already published a book or exited their first company or nabbed a grant for some important research. You’re younger or newer or less known.

I have often made foolish mistakes in these meetings. I want to help you avoid two of those that are especially common for the typical Leaflet reader (an earnest, principled, good-hearted person aka not a jerk).

The first one I call the “nice young man” mistake.

In the meeting, you don’t establish your bona fides. You have some kind of credential or qualification or accomplishment that would help this person situate you and take you seriously. But you leave it out, usually for fear of sounding pompous. It’s as if you submitted your resume but erased the best bullet points on it. 

When you make this mistake, the other person can come away thinking “well, that was a nice young [man]. On to the next thing in my day!” instead of thinking “this is someone I’m excited to support/sponsor.”

The second is the “no pitch” mistake.

This person is probably busy. Even if their calendar is loose, their mind and heart have plenty to occupy them. If they’re meeting with you in the first place, they want to be helpful. Make it clear and easy for them to do that. Ask for something that you want.

Here’s a list of things you might ask for:

• More of their time (make this easy: offer to calendar it, make it specific)

• Money

• Introductions

• Things you should read / listen to

• Feedback on a work product of yours

• A chance to shadow them for a meeting or a day

Asking for something and not getting it now, this time, doesn’t mean you failed. It doesn’t mean you’ve made a bad impression. It doesn’t mean you look grabby or grifty.

Pick up the tab, thank them with confidence, write a follow-up thank you note (longhand if possible).

-eric

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IN THE GAME FOR THE RIGHT REASONS

Unlike being smart or smooth, being in the game for the right reasons might not be discernible for your audience right away. Their intuitions and biases may give them the wrong sense of this about you - they associate your haircut or race or clothes or diction with motives/principles they think are not the right ones. So it’s not a bad thing and maybe even an important thing to say “I’m in this for the right reasons. In my view, those reasons are [reasons].” You might illustrate this with a principled choice you’ve made, a tradeoff you’ve accepted along the way. Maybe you did a version of this job for free (for the love of the game).

I’ve worked with political candidates who are policy wonks - they are good-hearted geeks who care a lot about the details of financial instruments and regulatory drafting and interagency cooperation. This kind of person places a premium on smarts. Intellect is probably one of their competitive advantages, or at least has been for long seasons of their life. 

These candidates worry about looking and sounding smart enough. I found that this worry led them to make mistakes. They overdid it on policy detail and sophistication. Their anxiety about their core competency - the thing they were obviously strongest at - blinded them to other harder things they needed to accomplish. For the audiences they addressed, the “is this person smart enough?” bar was usually met in the first couple sentences that came out of their mouths. Those sentences probably had semicolons and dependent clauses in them. 

The thing the audience needed to be reassured about was something more like “does this person get it? Are they fired up about the most important thing? Are they in the game for the right reasons?” I suspect those questions mask one underneath: “do they share my values?”

This can sound naive or guileless to some: if the person you’re talking to doesn’t even care if you’re in the game for the right reasons, you might want to minimize how much you depend upon them. You might not be that helpful to each other. When the sh*t hits the fan, you’re likely to prefer very different choices.

-eric

Read the rest here.

COMPELLING QUOTES

Writer Paul Hoover on memory:

We drag expensive ghosts through memory’s unmade bed.

Sales expert Chet Holmes on rapport:

When you sell, you break rapport, but when you educate, you build it.

Poet Wendell Berry on form and confusion:

It may be, then, that form serves us best when it works as an obstruction to baffle us and deflect our intended course. It may be that when we no longer know what to do we have come to our real work and that when we no longer know which way to go we have begun our real journey. The mind that is not baffled is not employed. The impeded stream is the one that sings.

Keep going, keep growing,

Ben & Eric