How to Get Your Boss to Say “Yes,” Part 3

The ability to sell an idea or project to your boss is critical to your success. If you can’t get your boss’s approval when you need it, you are not going to go very far in your career. In this three-part series I share six steps for doing it more effectively. In this post, I cover the last two steps. (You can find Part 1 here and Part 2 here.)

In my last post, I wrote about how to prepare to make a presentation to your boss. To get him to say, “yes,” I encouraged you to prepare a brief, written proposal. I even provided a template.

Woman Giving Her Approval on a Proposal - Photo courtesy of ©, Image #2437760

Photo courtesy of ©

Once you’ve done that, it’s time to anticipate objections and formulate talking points for each one. Don’t risk getting a “no” because you haven’t carefully thought through the questions and your responses.

Step 5: Make the Pitch

Schedule a time to make the pitch. Pick a time when your boss is likely to be the most receptive.

Has it been a bad month? Don’t schedule an appointment right after he’s likely to get the news. Is he more alert in the morning or the afternoon?

Use some common sense and try to schedule the meeting when you have the best chance of success.

Now go in and make the pitch. I usually just slide the RBF across the table and jump in. I literally walk through the document one section at a time.

Here are a few pointers to keep in mind while making your presentation.

  1. Maintain eye contact. I said that I walk through the document. However, I don’t read it. The document is intended to be a “talking points” list rather than a narrative.

    You should be familiar enough with your recommendation that you can stay focused on your boss—and his reactions—rather than the RBF.

  2. Stay alert to the signals. This is “Selling 101.” Does your boss appear bored? Pick up the pace. Does he have a question? Stop talking and let him ask.

    Hint: If your boss engages you in a discussion, this is a good thing! It means he is interested.

    Is he distracted? Let him get refocused or reschedule the appointment. The last thing you want to do is plow ahead, oblivious to the reactions of the very person you’re trying to persuade.

  3. Re-state the recommendation. When you get to the end of your presentation, restate your recommendation and ask for a decision.

    Then—and this is critical—stop talking. Give your boss a chance to say, “yes.”

    This may make you feel uncomfortable, but, trust me, you will decrease your chances of success if you keep talking at this point.

    Sometimes, your boss just needs to sit there and absorb your pitch. Sometimes, he may sit quietly to see what other information you may volunteer. Regardless, resist the temptation to fill the vacuum with words.

  4. Know when you are done. Once your boss approves your recommendation, it’s once again time to shut up.

    My Dad taught me this early in my career, and it has served me well ever since. I can’t tell you how many times I’ve seen a person in authority give his approval and then watch the presenter proceed to unsell the sale.

    If possible, when the boss says, “yes,” thank him for his decision, collect your belongings, and leave the room. If you can’t leave, then at least move to the next agenda item or change the subject.

Own the Outcome

Earlier in my career, I used to hear my peers constantly complain about how unreasonable their boss was or how bureaucratic the company was. Blah, blah, blah. They had a thousand-and-one excuses for why they didn’t “make the sale.”

Few of them were willing to accept the fact that:

  • Their proposal just wasn’t that compelling.
  • Their presentation skills sucked.

It was easier for them to blame someone else rather than accept responsibility for the outcome. As a result, they missed the opportunity to improve their skills.

If your boss says, “no,” go back to your desk and engage in a little postmortem analysis.

  • What went wrong?
  • What was missing?
  • What could have been stronger?
  • Where were you unprepared?
  • How can you do this better next time?

Accept full responsibility for the outcome, and you will gradually get better at this critical skill. Not only will you become better at getting to “yes,” you will also find yourself moving along faster in your career.

Question: How have you done in getting your boss’s approval when you need it? You can leave a comment by clicking here.
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  • Joe Lalonde

    For me, it’s been fairly easy. The problem has been getting a quick response. It’s been a game of asking, reasking, and asking again.

  • Joe Abraham

    I especially like #4. Sometimes it’s easy to be so carried away that we tend to share things that may not benefit both the parties. Yes, we got to learn when to shut up! 

    • Tim Peters

      It is not easy! Very thin line. 

      • Joe Abraham

        True, but still there IS a line! :) 

  • Thad Puckett

    Excellent advice.  I especially like the part about stopping talking once the pitch is made, and especially if you’ve received a “yes”.  

    Post mortem?  Excellent advice.  I think of it as a “debrief” and think it should be done after any significant interaction with boss, client or vendor, ideally with someone else who was there if possible.  It’s easy to miss things, and thinking through what just transpired helps immensely.

  • Rob Trenckmann

    For me, the hardest part of this is being silent after the ask.  It’s the same with raising money–I want to fill the silence.  But, letting them respond is so important.

    • Michele Cushatt

      I’m with you. I tend to think someone’s silence means I need to do more persuading. But I’ve learned some people need silence to think through the proposal. My talking just gets in the way of their processing.

    • Jason Stambaugh

      I tell people all of the time that people will almost never change their mind in the middle of an ask they are already want to say no to. However, if your pitch is rock solid, that silence gives them the chance. 

  • Dave Anderson

    I really worked at finding the WIFM (what’s in it from me) points in each section of my proposals.  If my boss did not realize a benefit in the proposal then it probably would not become a priority.

    I had good bosses who were servant leaders for the most part.  But, don’t take for granted that they see how your proposal can help them.  You must communicate it.

    • John Tiller

      Great point, Dave.  It’s always good to remember that everyone is tuned into radio station WIFM!

  • John Richardson

    Being prepared certainly helps. Another thing I’ve found is to find key people that your boss trusts and get buy in from them. If your boss has a consultant, confidant, or subordinate that they refer to when making decisions, running your idea past them first might give you a step up.

    • Michael Hyatt

      This is huge, John. I couldn’t agree more.

    • Michele Cushatt

      Great point, John.

    • John Tiller

      So true, John!  To dovetail on that:  If the circumstances allow for it, buy-in from their spouse almost always ensures a homerun. 

  • Tim Peters

    Michael – Great post and great to meet you at Catalyst. Know When You Are Done – Yes. I once had a team member propose a solution to me. I loved the solution and gave her several soft “yes” comments. However, she continued and continued to the point where I was no longer interested.  I then went backed and pointed out this fact to team member for her benefit in future meetings. Thanks. 

  • Matthew Reed

    one of the things that Patrick Lencioni talks about is the fact that often the ability to be fully heard (in the context of a team) is enough. 

    Your comment on ‘own the outcome’ made me think about this. If the ‘boss’ has genuinely done a good job at developing a team then the ‘no’ is more palatable.

    • Michele Cushatt

      So much of what happens within the context of a 15 minute meeting actually happened in the weeks and months leading up to it. It’s rarely about those short 15 minutes alone.

  • Andrew Chalmers

    I think one of the most crucial things I have learned is to pick the best possible time to pitch ideas. Sometimes I will be excited about the idea in a moment when I receive great news and want to tell him as he is walking into the office. I have learned that at that moment I am less likely to really have his attention. Now I strategically plan when I meet with him to give myself the best opportunity when presenting ideas.

    • John Tiller

      So true, Andrew!  Waiting also gives me a chance to better prepare for objections that I haven’t even thought of when I first get excited about the idea.

  • Wayne Stiles

    Even when the boss says, “Yes,” it may be wise to wait 24 hours before moving too far with the permission. Sometimes a genuine “yes” may be retracted after the boss sleeps on it. 

    • Michele Cushatt

      Either that, or move forward as fast as possible. Like snapping the football before the challenge flag is thrown. ;)

      • Wayne Stiles

        Ah, yes. But not all officials play by those rules. :-) Some throw flags any time they choose!

      • John Tiller

        That’s right, Wayne and Michele!  

        If the boss gives you a check, run  straight to the bank and cash it.  If he gives you approval to move forward on something that will take a lot of your effort to un-do, begin work after he’s slept on it.  

  • Maurice F. Overholt

    I have learned to know my boss, elder board, or finance team as well as possible (preferences, focus, desired outcomes) before asking for something, and then to put my request in those terms.  Your posts, however, have helped me think more deeply about the proposal process.

    • Aaron Johnson

       So true, Maurice. Reminds me of Covey’s Habit #5 – seek first to understand, then to be understood.

  • Hilary Eledu

    Sometimes I succeed, and sometimes I don’t. This article is definitely going to greatly improve my success rate. Michael obviously shared his experience from the other side of management which makes this article practical and tremendously helpful.

  • Gary Morland

    Postmortem analysis. Accepting full responsibility for the outcome. Wow, like grownups or something.

    So when did you say these 3 parts would be a standalone thing we can get? Otherwise I got to copy and paste.

    • Michael Hyatt

      I am not sure what you mean. The series is in three parts. You can just read the first one then go to the next, etc.

      • Gary Morland

        Its a dumb joke intended to be a compliment. I think it’s valuable enough to be some kind of standalone resource, but I’m just being lazy to keep from copying and pasting. Seriously, it’s very helpful to me – specific, practical, complete. Something I’ll use right now. Appreciate it. Sorry to be confusing.

        • Michael Hyatt

          Okay, got it. Thanks for explaining. I probably needed another cup of coffee!

  • RoryPeebles

    Michael, I see several key points that I will incorporate when pitching my ideas. It is not uncommon for me to present ideas to people who are not my boss, yet they are decision makers or even in some cases potential employers. I intend to utilize your template going forward.  Are there additional strategies you would recommend when selling ideas to non-boss-decision-makers?

    • Michael Hyatt

      What i have shared in this series will work equally well with clients and other “customers.” Thanks.

  • Joseph Michael

    Thanks for this great series. Perfect timing as I have quite a few things I will be needing to discuss with my boss so this information is really helpful. I can’t wait for the day when I am able to be my own boss. I happen to know how to get myself to say yes rather well :-) 

    • Jason Stambaugh

      Saying yes though, for some reason, is a little scarier when you are the boss. As a small business owner, when I say “yes” to something, that typically means I’m the one who has to do the work…

  • Pingback: How to Get Your Boss to Say “Yes,” Part 2 | Michael Hyatt()

  • Travis Dommert

    Do you ever recommend simply not taking ‘no’ for an answer?  

    Risky, but I have seen conviction (and volume) change leader’s minds.

    Potential breakthrough or CLM (career limiting move)…?  

    Of course, those were also people who preferred to ask for forgiveness rather than permission!

    • Michael Hyatt

      It all depends on the boss, your credibility, the issue, and the circumstances.

    • Jason Stambaugh

      I’ve heard of some epic stories, but I’ve always found that is best to put the matter on the shelf and dust it off at the next opportunity. Diplomacy…

  • Aaron Johnson

    I’m grateful to have a really receptive boss. One thing I’ve found is that a “no” doesn’t necessarily mean “never.” If your proposal is a good one and clearly connects to your boss’s/company’s goals, it’s likely that your ideas will haunt your boss (in a good way), and she may ask to revisit your proposal.

    The possibility of this is a good reason to keep things brief and clear.

    • Jim Martin

      Very good point, Aaron.  You are right.  “No” doesn’t necessarily mean “never.”  Understanding this might lesson the frustration when the outcome isn’t necessarily what we would have preferred.

  • Dan Erickson

    The communication department at my college lost an instructor to retirement last year.  Due to budget cuts the the president decided to put our position and an opening due to retirement in the music department on hold for a year.  This year our dean says we’ll be lucky to get one of the two positions back.  I have to develop recommendations and arguments for the dean to take to the president to convince her to hire a communication instructor.  Your advice is sound.  I especially like #4: “know when you are done.”  I’m a proponent for being short and concise with a strong argument.  

  • Yasue

    My bosses are located in other countries. I hope you can cover the similar topic for people in my situation, no business trip, rare Video Conference interaction but telephone/email only.

  • Ed Ollie, Jr

    Thanks Michael! I have often heard people use the phrase “Leading Up”, but I’ve come to believe there is no such thing. It is possible to lead by influence, as a superior has no desire being told what to do by someone they lead, especially if you haven’t been around long. Influence denotes relationship, trust, and the ability to speak into the process. I’ve found this to be a critical skill that always pays direct rewards toward a “yes”.

  • Delores Liesner

    I found it interesting that most of these steps are similar to those I recommend for conflict resolution or workplace disciplinary response.  With that thought the points could apply to any relational situation where negotiation is needed.

  • Gregory Speck

    Thank you for this post, Mr. Hyatt!  I used the template to create a commission structure and receive a bonus.  The bonus I received due to the template you shared was $500 more dollars and 2 months earlier.  I thank you and my family of 5 (3 children 3 and under) thanks you!
    Bless you,

    Gregory Speck

    • Michael Hyatt

      Awesome, Gregory. So glad to hear it.

  • Alex Barker

    I used some of your techniques for a proposal to my boss. And she accepted it! Thank you for your suggestions. 
    My only advice to become a go-getter, I believe that is what truly helps me

  • cristi

    I think we have to take care about the culture and nationality of the boss.
    If he is french working abroad is different like approach