Good Managers Never Say “Yes”

Being Mindful and Effective Means Don’t Assume, Ask

Jonathan Rosenfeld
5 min readAug 6, 2014

Requests are almost always just the tip of the iceberg

This is a pretty simple perspective depending on how you look at requests in the first place. We can think of all behavior—going to a conference, moving one’s desk, leaving a work team—as problem solving activity. A request to take action means the person reporting to you has constructed a solution. To effectively manage, one needs to know the problem behind the solution. For example, Anna might want to move her desk because she has an unresolved conflict with Xiao. Exploring the problem can lead to radically different solutions. Maybe Anna needs help with interpersonal skills. Maybe Anna and Xiao need tighter direction for working together. Or Maybe Anna and Xiao are good, and she just wants a desk closer to natural light.

The price of saying yes is high

If you just say yes to a direct reports request, You may never find out the actual problem your report is trying to solve. To best manage people you need to know what inspires them, as well as their concerns. The back story behind the solution lets you learn about their problem solving strategies. Good leadership is dependent on gathering data. If time allows, you never want to take a pass on finding out who your people are.

Smart, busy people make reasonable assumptions. Let’s take a simple example to illustrate this.

Tony a young and inexperienced designer sends you a request to attend a local conference on how best to use fonts. “Excellent,” you think. You assume that Tony’s taking initiative, honoring the office norms of everyone going annually for training. You've been thinking that Tony needs to pick up skills that complement the rest of the team, “and this fits the bill.” Better still, Tony has picked a relatively inexpensive conference. You're pleased at the total cost and its impact on your training budget. It’s good to see what a sensible, frugal, and aspirational person Tony is turning out to be. This just validates your judgment in hiring Tony in the first place.

Given how busy you are, you’re pleased to give a quick thumbs up to this excellent request. You assume that Tony put a lot of thought into this, did his homework, conferred with senior colleagues. Maybe you even go so far as to assume that this is evidence of the excellent relationship you have with Tony. You think, “The rapport between Tony and I is so strong, that we are on the same page without even needing to have a meeting.” You feel validated for all the good efforts you’ve put into being the best manager you can be.

“As a thought exercise,” let’s consider the possibility that all your assumptions, while reasonable and sensible, are way off. Let’s say you take the time—and have the skill—to draw out of Tony the story behind the solution.

Maybe it turns out that Tony has been in a panic, watching one person after another go off on annual training trips. He’s discreetly inquired and is shocked to hear how expensive conferences can be especially with airfare and staying at “fancy” resorts.

Tony makes 65K annually, comes from a working-class background, and finds it implausible that the company is truly willing to invest thousands of dollars in his professional development. He feels so inadequate in so many skill areas, he still can't believe that the company hired him. He’s anxious about every conversation with you. He’s been waiting to hear how deficient he is and how you have to let him go. He’s working hard and trying to stay under the radar. Tony doesn't want to be the only one on the team who hasn't gone off for annual training. He doesn't want to be seen as a poor team player or as someone who’s not aspirational.

Just this morning Tony got an email telling him about this Font conference right down the street. It’s really inexpensive and looks legitimate. He’s so relieved. He can go to a conference and then come back to the office each evening. Once you approve, he’s planning on letting you know that he’s happy to skip some sessions if there is pressing work.

Solving the wrong problem is expensive

What was the problem Tony was trying to solve? It certainly wasn't skill development. Existentially, it appears that Tony is grappling with what people like to refer to as impostor syndrome. The is an almost universal affliction for the young and inexperienced in their first job. For many it becomes a lifetime chronic condition. How many companies squander massive resources treating this condition, while ostensibly working on skill development?

Solutions owned by you and your report have the most punch

Imagine you have a thoughtful conversation with Tony, and he’s able to express his hopes and fears. You in turn are able to give him your seasoned perspective: “We knew you were a novice when we hired you, and we're not holding you to the same standards as people with five to ten more years experience.” Not to mention, you really do want Tony to acquire new skills. You know this is most likely to happen if he pursues what truly interests him.

Ideally you'd be able to draw out of Tony what he’s really interested in, and together the two of you could identify a conference that is an excellent fit—and reasonable in cost. You might reframe the whole experience. As in, “Tony, you have a responsibility to the company to build your skill set and to acquire skills that will make everyone around you better. Going to the wrong conference, while not giving it your best attention, is a poor use of company resources.”

What are some potential unintended consequences

Good managers risk discouraging and destabilizing their reports when they don’t say yes. The most important part of not saying yes, is not saying no. The language one uses is that of clarification and exploration. Leading with: “Thanks for taking the time to put together this proposal” and “Let’s talk about this. I want to make sure this is the best fit for you.” It’s always good to use authentic and affirmative language.

Even in a good clarifying and exploring conversation, there is the risk of your report feeling misunderstood and micro-managed. They might even find your questioning invasive and inappropriate. It’s helpful to use meta-comments, which I like to call process comments. You might say, “Tony, it’s not my intention in this conversation to question your judgment in picking this conference. I want to be as effective a mentor as I can be. I want to build a bridge between you knowing yourself and what you want to do, with my broad experience in the field, including having been to many a great and many not so great conference. Let’s put our heads together and see what we come up with. Will you work with me?”

Going slow to go fast: means don't assume, ask

Of course good managers will often say yes. But it’s good to be mindful. It’s critical to find out what’s really up with the people who report to you. Reports are less likely to be defensive when you ask them to “deconstruct a request,” than an out-of-the blue, without-context, “so how have you been doing?”

It’s an excellent investment of time to slow down, and respectfully explore people’s thinking. When you understand your people you can validate their process of analyzing and solving problems, or guide them to more robust solutions. Respectfully questioning your people is a highly effective way to frame yourself as mentor, which contributes to people's sense of wellbeing and engagement at work—factors highly correlated with productivity and retention.

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Jonathan Rosenfeld

VP Coaching & Executive Development @ StockX: Mindfulness, Change Strategy: