Dont Bring Me Problems, Bring Me Solutions

“Don’t bring me problems, bring me solutions” is a common message that one imagines a stereotypical CEO saying to their teams. While this literal phrase isn’t particularly common in the wild, it’s rooted in some deep underlying truths about communication with executives. In this post, we’ll dissect this catchphrase as a means of analyzing how to effectively communicate upwards, whether to a senior manager, head of function, or CEO.

Why Effective Communication With Executives Matters

One of the very best parts of working at a startup is that you get to work closely with your company’s leadership team. Startups are small and everyone works together, and if you’re a strong performer there are often very direct routes to directly collaborating with or becoming a member of a company’s senior leadership. Because of these opportunities, it’s wise to make sure that you can communicate upwards effectively.

There are obvious benefits to communicating well. You’ll sound smart, and if senior teammates think you’re smart they have the resources to promote you faster or compensate you better. People in high-responsibility roles also tend to have more leverage to help (or harm…) the business overall, so communicating with them well is a good way to get things done for everyone’s sake.

Being able to communicate in a way that matches executives’ expectations is also a very useful skill for people who are ambitious, because among other things this is how senior leaders talk to each other. If being a CEO is in your future, these skills will help you work better with future peers or board members.

Don’t Bring Me Problems, Bring Me Solutions

Context Switching

Senior leaders need to context switch a lot. At a startup, it’s hard to find focused blocks of time to work; at a larger company it’s often nearly non-existent. I’ve spoken with executive coaches whose primary role was essentially just organizing CEO schedules in order to carve out just a few hours of focused thinking per week (think 5-8 hours total across 6 work days).

The day-to-day experience of working in a fast-paced environment is a little bit like playing dodgeball without your glasses, with new issues getting constantly thrown in your face with little warning. This isn’t some woe-is-me situation – it’s the nature of the job and there’s absolutely no problem with it. But it dramatically reduces the cognitive bandwidth that people with large teams have available to pick up a novel problem. It is much easier to pick from choices that have been laid out in front of you, rather than inventing a new solution from scratch (“Bring me solutions”).

That said, effective executives can handle open-ended problems and in fact are getting paid to do so. You can bring very heavy and amorphous problems to good executives, but what you bring should consist of specific problems framed with a high degree of context, and clear criteria for resolution.

When setting context for a senior audience, you want to act as a magnifying glass that focuses on the most relevant information about a problem area, not just a window that shows everything. Doing this well will make you seem smart and help you get what you want from conversations, whether that’s advice, resources, or simply a better informed boss. Not setting context or setting it poorly will generally get you the opposite.

Some of the best ways to be concise and structured about context setting are:

  • Always prepare a shared written agenda for any meaty topics that you want to bring to a one-on-one
  • Learn to get good at concise communication of complex situations: When in doubt I recommend something like the Goal-Problem-Solution system we’ve written about before
  • Learn to separate accuracy from completeness. You don’t need to tell your CEO every single detail of a 6 month project – you need to give them an accurate view of what happened, with 100% of the relevant details and no others
  • Build business knowledge. One of the worst patterns that leads to unclear communication is a missing sense of priority where people frame low priority speed bumps as high priority emergencies

Consistent Initiative

One of the reasons that there’s so much value in the concept of bringing someone solutions rather than problems is that it inherently demonstrates initiative: There’s a problem, and even if it’s bad, we at least have a plan to solve it. Executives love when people on their teams take initiative, because proactive teams don’t require as much attention, and teams that don’t require much attention allow them to context switch into their domain less.

You should strive to always show how your team already has forward momentum (or your own personal plans, if you’re an individual). That puts your area of responsibility firmly in the camp of “be aware, course-correct if necessary” rather than “I need to personally instigate change” which is inherently not what execs want to do. The more initiative you take, the more room for initiative you’ll be given.

Politics and Executive Communication

The final lesson to draw from the concept of bringing solutions rather than problems is that following this advice will inherently make you less political. This is a good thing.

There’s a class of “problems” related to workplace politics that will essentially force you to bring up a problem without a solution. For example, “I should run this project, not [rival],” or “[other team] doesn’t know what they’re doing.” Executives hate it when you drag them into your politics, for several reasons.

First, most executive compensation structures are set up to reward whole-company performance. Many execs receive performance bonuses based upon growth, revenue, and profitability; key CEOs often have massive equity boosts based upon hitting stock price milestones; and on the other hand, senior leaders can be fired for failure to hit targets (even when it’s arguably not their fault!). So while they themselves may unfortunately get distracted by politics, they’d really prefer if their teams didn’t.

At the same time, it’s hard for most people to detect all but the most obvious political activities happening junior to them in the org chart. Half of the politics game is presenting a rosy upward picture; as a result one only sees the outputs of politics at layers below them.

The combination of these factors means that bringing your political baggage to someone more senior will usually be both surprising and upsetting. It will be surprising since they’re probably not deeply aware of the state of the team’s internal dealings. And it will be upsetting, because it means that people have been messing around posturing instead of, you know, actually doing their jobs.

I’m not here to say that you need to entirely avoid politics, because realistically unless you’re the CEO you probably can’t. And I’m not here to say that any of this is right or “fair,” because many execs are themselves unfortunately highly political. But you should definitely avoid bringing politics into conversations with people senior to you in the org chart.

Final Thoughts: Try Your Best to Be Positive

One thing that I find many people don’t realize is that if you’re an executive who is doing your job, you hear a lot of bad or unpleasant news in a given week. Generally speaking bad news bubbles up due to a confluence of factors ranging from escalations of conflicts, to sharing of confidential information, to people simply covering their asses.

This gets even more extreme with certain roles like CEO, General Counsel, Chief People Officer, or CISO, where almost everything that’s put on your plate is bad, and some of it is both bad and scary:

  • We’re getting sued
  • We had a major security breach
  • Our CTO is resigning
  • We had a major HR issue at a company function

Different personalities handle this stream of bad news with varying levels of skill, but everyone that I’ve ever met, even the most unflappable, finds it tiring at minimum. It’s just human nature. People would rather be surrounded by positivity than negativity, even if it’s their job.

To be more effective when communicating with executives, try not to be one more boxcar in a train of shitty news that someone has been inundated with. One of the best ways to make sure that you’re getting the most out of executives is to be someone that they’re excited to hear from. I’m not saying that you should hide bad news, but there is value when communicating with senior leaders to being what I’d call “emotionally optimistic.” Try to avoid bringing in bitterness, defeatism, or cynicism. In addition to this just generally being a nicer way to live, it’ll also help you bolster someone who presumably is pretty important to your career.

This is doubly true if you are a senior leader yourself. If you’re a VP or beyond, you’re far too senior to treat your boss as your therapist. If anything, you should be an emotional shock absorber for them. Help to distribute the total stress load on the company by taking on a bit of it yourself.