Although people tend to make many types of assumptions, one of the most common assumptions I observe is when we try to guess what people want. All this guessing has a significant impact: it wastes time, escalates tension, and causes unnecessary stress. Fortunately, there’s a simple solution: we can stop guessing what people want and ask them.

Playing the Guessing Game

Consider what the assumptions might be in these real-life scenarios:

  • An employee continually tried to please her boss. She put in a lot of extra hours, tore her hair out re-writing draft after draft of everything she wrote, had her phone on at all times, and gave her boss status updates every day.
  • A team was working on a major presentation for an idea to pitch to senior management. They collected facts, figures, and an abundance of financial data and statistics because they thought it would convince management to support their idea.
  • A young employee had major career aspirations. He took every training he could, constantly networked, and looked for opportunities to show off his accomplishments to people in the company who he thought might hire him.

You might be thinking, “OK, so what? These are things that most employees should be doing. What’s the problem?” The problem is that, in all three cases, each person was making incorrect assumptions and trying to guess what others wanted.

The Truth Behind Assumptions

Let’s look at the assumptions everyone was making in the above examples:

  • For the employee who was trying to please her boss, the boss doesn’t care that much about extra work and minute details. In fact, the boss appreciated employees who strove for a work-life balance and spent time with their families. The boss also appreciated people who presented new ideas and who were willing to respectfully question her ideas. Because the employee was focused on pleasing, she never stopped to notice what the boss really wanted.
  • In the team’s presentation, although senior management appreciated some data, what they really valued were case studies and anecdotes. They don’t want numbers thrown at them – they wanted to engage and dialogue with the team. It was important for them to get a sense that the team could tell a story to engage people, not bombard them with data. Senior management didn’t buy into the idea.
  • The young employee didn’t realize that there were many steps he needed to go through to even get close to the position he wanted. Because of his lack of experience, it would have taken him years to get to the position he wanted based on tenure at the company. Although he was learning useful skills, they weren’t directly relevant to what he needed to learn based on his position and his pushiness turned people off.

I frequently see people make assumptions like these. They spend a lot of time putting energy into what they think people want, only to find out that they were way off course. Or, even worse, they never find out and make even more assumptions around how difficult or wrong the other person is.

A Simple Way to Stop Making Assumptions

How can we stop engaging in this dance? It’s simple:


Ironically, perhaps because it’s so simple, many people don’t even consider it. I’ve seen people literally try one failed strategy after another because they keep trying to guess what the other person wants. Eventually, they either give up, the relationship gets strained beyond repair, or they stew in feelings of resentment and bitterness.

Instead of going around in endless circles, you have a choice. When you embark on a new project, relationship, or role, you can initiate a conversation and ask what the other person is looking for and what their expectations might be. Ask enough questions to make sure you’re clear. Along the way, if it seems like you’re off, you can go back and ask again until you get on track.

The same works in reverse: you can also state your expectations and what you’re looking for with people who work for you. This will prevent them from playing the guessing game and ensure you’re on the same page.

If you do find yourself trying to get someone’s approval, buy-in, or meet their expectations without success, consider that you’re probably making assumptions about what they want. This is a good clue to have a conversation before going any further.

Alternatives to the Guessing Game

Let’s go back one last time and look at how asking these questions would have saved everyone a lot of heartburn:

  • The employee could have sat down with her boss and asked the boss to share her standards and expectations. She could have shared what she wanted (to please her boss, get a promotion, excel in her job) and asked the boss how she could accomplish those things.
  • The team could have asked someone from senior management (or colleagues who presented in the past) what kind of information and style they look for in presentations. They could have asked what criteria management uses to make decisions, then designed their presentation to showcase that information.
  • The young employee could have shared his goals with someone from HR or a similar department and asked what path he could take to get there. He could have asked hiring managers what they look for when making hiring decisions and sought out leaders at the appropriate level for his next position.

Fortunately, you can avoid the guessing game and cut to the chase. Consider the following questions and take action:

  • Whose approval, buy-in, or expectations am I not successfully getting and what assumptions might I be making around what they want?
  • When thinking of supervisors, clients, or colleagues, what clarity do I need in order to give them what they want?
  • Who might be trying to meet my own expectations, wants, or needs without success? What information can I provide to ensure they are successful?