Introduction
People consistently expect more refusals than they get, and that misjudgment keeps good requests from ever being made. Learning how to ask for what you want at work starts with knowing the odds are better than they feel: ask directly, be specific, pick your moment, and treat a no as information about that one request.
Most professionals have a message sitting in their drafts. It might ask for an introduction, a raise, feedback on a project or a chance to lead something new. Juan Bendana has written that courage can be as small as sending the email you've rewritten six times. The rewriting usually comes from a prediction about how the other person will respond, and research suggests that prediction is more pessimistic than reality.
The Gap Between What You Expect and What Happens
In a series of studies published in 2008 in the Journal of Personality and Social Psychology, "If You Need Help, Just Ask," Francis Flynn and Vanessa Lake tested whether people underestimate how likely others are to agree to a direct request for help. In the first three studies, people underestimated by as much as 50 percent how likely others were to say yes, across a range of requests in both lab and real-world settings.
The participants who went out and asked strangers for help were surprised by the results. As Lake later put it in an interview, they came back saying they couldn't believe how nice people were.
Why the Person You Ask Sees It Differently
Flynn and Lake traced the gap to perspective. People who are asked for a favor feel social pressure to help, because saying no can make them look bad to themselves and others. People planning to ask underestimate that pressure. Askers believed it would be much easier for others to refuse than the people being asked actually found it.
That misjudgment also pushes askers toward indirect approaches that work worse. In one study, askers believed they'd get more help by being indirect, such as signaling with a look, while the people in the helper role said they were much more likely to help if asked point blank. In another, participants wrongly predicted that handing someone a flyer would get more questionnaires filled out than asking outright.
Flynn's takeaway is to pay more attention to how your request is made than to its size. That fits Juan's note that a clear request gives people something they can say yes to.
Being Asked Feels Better Than People Think
In a 2022 paper in Psychological Science, "Surprisingly Happy to Have Helped," Xuan Zhao and Nicholas Epley found that people also underestimate how positively others feel about being asked. Helpers were more willing, and felt better about helping, than the people asking expected.
Their work extends the earlier findings. People asking for help underestimate both how likely a yes is and how much a request can be a positive moment for the person on the other side.
Asking for Advice Can Make You Look More Competent
A common fear about asking is that it signals weakness. A 2015 study in Management Science by Alison Wood Brooks, Francesca Gino and Maurice Schweitzer, titled "Smart People Ask for (My) Advice," found that seeking advice can raise how competent the advisor judges the person asking to be.
The effect was strongest when the task was difficult and when people asked advice of the same person who would be evaluating them. On easy tasks, the boost was smaller. So for a request like feedback on a complex project, or guidance from a leader a few steps ahead, the research gives a reason to expect asking to help your standing.
What a Past Refusal Does to the Next Request
In a 2014 set of four studies published in Social Psychological and Personality Science, "Once Bitten, Twice Shy," Daniel Newark, Francis Flynn and Vanessa Bohns looked at what happens after someone has already said no. People seeking help tended to underestimate how likely the same person was to say yes to a later request, because they didn't grasp how uncomfortable it is to refuse someone twice.
A no on a raise or a stretch assignment tells you something about that moment: the timing, the budget, the priorities. A better-timed request may get a different answer.
Where the Research Stops
The requests in these studies were mostly small ones: favors, questionnaires and donations. A raise or a promotion involves budgets, approvals and constraints that even a willing manager may not control, so these findings can't tell you the odds of a specific raise request.
The pattern they reveal is still useful. Across many studies and settings, people consistently misjudge how likely a direct request is to get a yes, which makes staying silent less safe than it feels.
How to Make a Request That's Easy to Say Yes To
The studies point to a few habits:
Ask directly. In person or by voice where possible, instead of hinting.
Be specific. Say what you want, why, and by when, so the other person can answer without guessing.
Pick your moment. Time the request with the other person's constraints in mind.
Treat a no as information. Learn what it tells you about that request, then come back with a better one.
These habits are a practical reading of the research; the studies didn't test them as a set. If the hard part is working up to the ask, it can help to talk to yourself the way you'd coach a friend before they hit send.
What Leaders Can Do
The misjudgment runs the other way too. In a 2010 study in the Journal of Experimental Social Psychology, "Why Didn't You Just Ask?", Vanessa Bohns and Francis Flynn found that potential helpers underestimate how uncomfortable it feels to ask for help, so they overestimate how readily people will come to them.
For leaders, that means waiting to be asked may mean waiting a long time, while people on the team hold back requests they'd be glad to make. Inviting requests directly, with a standing offer to talk about raises, development or introductions, lowers the barrier.
Help Your People Make the Ask
Juan Bendana's Confidence Cycle keynote is built on the idea that action comes first and confidence follows, and sending the request is one of the most concrete actions a professional can take. It fits leadership conferences and corporate events where people hold back on asks that would help their careers, and sales kick-offs where reps need to ask for the introduction, the meeting and the close.
Talk with Juan Bendana's team about helping your people make the asks they've been putting off.
The request you keep rewriting has better odds than you think.