Five Truths to Improve Hard Conversations with People in Power
The delightful fantasy novel The House in the Cerulean Sea features a good-hearted bureaucrat’s struggle with his organization’s leaders, known only as Extremely Upper Management. This week I’m going to talk about how to have successful conversations with people above you in the hierarchy and I’m focusing on Extremely Upper Management. The advice mostly also works as you move down the hierarchy, so if you’re an individual trying to talk with your first line boss, or a middle manager you’ll still find useful stuff here.
I have a distinctive perspective on working with people in power because of the shape of my career. In 2009, I’d reached director level in my product engineering organization, regularly working with VP’s, our CTO, and other executives. Then I switched to part-time project management work so I could start writing fiction. Moving back to full time work, I worked as a project manager and then found my home in product management. In seven years, I worked my way from Product Manager to Chief Product Officer. Working as an individual contributor (IC) after being in a leadership role I watched leaders through the lens of my own experience. I saw clearly how different it sometimes was to work with leaders as an IC. When I moved back into management roles I tried to apply my new insights and find ways to bridge the organizational communication and power gap.
I think these articles are the most useful when I talk frankly to give you the world as I see it. These facts aren’t excuses, and I’m not asking you to feel sorry for executives. I think understanding these realities can help you prepare for and have better hard conversations.
1. Leaders are evaluated differently
Once you manage people the way you are perceived and valued changes. Your team is now the primary measure, not your individual knowledge or achievements. You are expected to hold your team accountable and probably have goals to make them more effective or productive in some way. After all, most teams aren’t perfect, any more than people are. You can’t expect a leader to always defend their team; they need to be discerning about when to push and when to protect.
Some organizations practice the concept of a “first team.” This means that a manager’s first loyalties are to their immediate peers, not to the people who work for them. In other words, your boss’s first team would be all the other managers who also report to your grandboss. This means they are working to optimize outcomes not for the team they manage, but for the next level up. Even if that’s not the culture in your company or organization, competent management folks are definitely spending part of their energy making sure they have solid relationships with other leaders in their organization.
Good leaders also very much care about their team and want to help them. Be aware they are pulled in both directions.
2. Leaders have different financial rewards
People in Extremely Upper Management often have a very different financial reward system that everyone else. This is true both in terms of what determines their pay and how much money we’re talking about. Some leaders have bonus targets that are specific to the areas they control. Some only have company wide shared goals, like sales or stock price. Some executives have some of each.
The way a company structures financial rewards tells people what they value. I worked at one place where stock grants didn’t vest until year two and three. In startup-land it’s common for stock to vest quarterly after an initial one year “cliff.” This can change how executives think about things. With a longer vesting cycle they may think more long term, but are also tempted to take fewer risks, as they need to stick around long enough to get paid.
In a typical Silicon Valley short-vesting cycle, execs might be motivated to move the stock price up quickly. It could make them favor short term wins over longer term value. In product terms, think about the tradeoffs of shipping new features or products vs. building a platform. Quickly building, testing, and if necessary, killing, products is going to be more in line with a short vesting cycle. It might be easier to sell the long term savings of building a flexible platform if the company is taking a longer view, but harder to get approval to move fast and break things.
Here’s what I mean. Let’s say one of the Chief Product Officer’s bonus goals is launching three new products this year. As the year goes on, the company has some reliability issues and the teams propose that they pause product work and work on reliability. Now the CPO sees the plus side of that pitch, but also knows that their pay, and maybe the rest of the exec team’s pay, depends on launching three products this year. That is putting weight on one side of the scale. But, don’t give up! Sometimes goals can be changed when circumstances change, and some execs are really good at finding a way to the right thing. But if you know that’s an obstacle going in, you’re going to have a more productive conversation.
I’m not saying that Extremely Upper Management only considers their pay when they make decisions. But they are, some more, some less, aware of it. And they didn’t get where they are without being very good at hitting the goals they were given.
3. You don’t have all the facts
Here’s another hard truth. Managers know things they can’t tell you. They know who’s on a performance improvement plan, who’s being investigated for suspect behavior, and who’s most likely to get laid off. Extremely Upper Management knows all kind of stuff they can’t tell you, from mergers and acquisitions to an upcoming reorganization to a huge customer deal that’s going to be announced next week that will change the product roadmap. And they’re also humans who might be looking for a job, or trying to get promoted, or are distracted while they wait for the results of a very scary medical test.
When you’re operating in this kind of unequal information economy, it helps to be patient. When you hear something that doesn’t make sense, don’t write it off, try to explore it and understand it more. If the other person seems reticent, ask if there’s something going on where it would make sense to wait a few weeks before continuing the conversation. If they’re engaging because they’re focused on keeping a secret, offering them a pause can be more productive than pushing.
4. You should talk privately
It can be very tempting to have conversations with Extremely Upper Management in a group setting. After all, they’re hard to to get time with, and here they are in this meeting that’s just you and five other people! But remember, we’re talking about a hard conversation, not feedback like “I loved the new brand video.” Most people would rather have hard conversations in private. Leaders can be more vulnerable and more open to change when they don’t have to consider who’s watching and what might news might get spread inaccurately through a game of telephone.
5. You should build them a bridge
When people in power take a position it’s usually well known. So changing a decision can be harder for them because there’s a lot more work involved to communicate the change, people naturally resist change, and leaders worry they will perceived as wishy-washy or weak. Here’s something you can do when you need a person in power to do something that may seem at odds with their past stance or decisions. Build them a bridge. Think about how they can position the change in the light of new knowledge or circumstances. If you build that bridge for them, so they can see how to communicate how they got from A to D, they’re going to be more receptive to change.
Consider the example above of the CPO with the goal to launch three new products. If you know that going in, you can suggest ways for them to sell updating the annual goals, or suggest a way to reduce the scope of the third launch to barely make it across the line.
Wrap Up
These facts aren’t innately good or bad. Most people in Extremely Upper Management want to do the right thing, most of the time. But because of their realities, you may find they need more data, more time to test things with their peers, or a better understanding of the downsides and upsides. Be curious, try to understand what’s important to them, how your topic fits with both their explicit goals and the social contract they’re working in. Steel yourself that things might take longer than you’d like and what you’d like to resolve in one conversation may take several more.
This was a complex article to write. Let me know what you think! Did I miss something? Do you disagree? I’ve got no power whatsoever, so lay it on me!
Your Dot Release: Think of someone above you in the hierarchy with whom you might need to have a hard conversation. It could your boss, or a great-grandboss, or it could be a leader above you in a different department. See how much you can suss out about how they’re rewarded. Identify two other senior they probably need on their side for them to be successful. Now, think of three things important to those two people. Congrats! Now you’ve got a bunch of new insight into factors they’re going to consider in a decision.
This is part of a series on hard conversations. Last time I talked about things to consider when you’re going to have a hard conversation with a peer.
Release Notes: Portland people, I’ll be facilitating a session on bragging for product managers at the Portland Product Tank on January 28 - that's tonight!. Jack Hott will also be talking about a practical use of Generative AI. I’m excited for both sessions as well as the chance to hang out with product folks. Event info and registration (it’s free!) are here: https://www.meetup.com/producttank_portland/events/305468076/?eventOrigin=your_events
The Dot Release is my newsletter for focused and actionable career, leadership, and product advice. You don't need a full upgrade, just implement a dot release! If you’d like to ask a question, just hit reply to this email, or drop a comment on the post. All articles are available for free and you can subscribe on my website.