Want a Promotion? 4 Ways to Get Your Boss to Always Say 'Yes'

There are three questions I get asked over and over again by friends and readers who care about advancing their careers.

  • How do I convince my boss to give me a promotion or raise?
  • How do I deal with a colleague who seems determined to F up my life?
  • How do I re-brand myself so people take me more seriously at work?
  • Over the next few articles I’ll go through each one of these to give you some tips that have served me well in my career so you can avoid some of the mistakes I made along the way. Let’s start with #1!

    How do I convince my boss to give me a promotion or raise?

    The phrasing of this question is actually a great place to start. More often than not the promotion question contains phrases that sound a lot like these:

  • How do I convince my boss to give me a promotion?
  • How do I ask my boss for a promotion?
  • How can I make my boss recognize that I deserve a promotion?
  • If you’re thinking about the promotion process along these lines i.e. as something you have to pitch, show or make your boss do, I’m afraid you’re already heading down the wrong path. In fact, the biggest mistake I see friends and colleagues make when it comes to promotions, is that they treat them as a point in time event - a binary decision or pitch to their boss. This strategy will get you nowhere.

    It doesn't help matters that so many career blogs and workplace columns focus so much time on the importance of bringing in data to support your case, preparing your pitch for a promotion etc. They’re all missing the point.

    The single most important thing you can do to get a promotion is to stop thinking about it as an event or a decision, and rather turn it into a journey you go on together with your boss.

    I've never asked for a promotion in my life but I've had several. As counter-intuitive as it may sound, when it comes to promotions, you have to play the long game to make them happen fast.

    So how does that work?

    When you frame your promotion as a journey, your boss can never say no:

    If I walk into my boss’s office tomorrow and ask him to promote me to President, I’m putting him in a very difficult spot. I’m unnecessarily forcing him into making a binary decision which will more than likely result in a “no”. There are just too many reasons for him to reject this style of pitch. The timing may not be right, there may be someone in the job already, the budget might not be there, and my skills might not be adequate. By forcing him to make a discrete yes or no choice, I’m inadvertently hurting my chances for a promotion and I’m also risking the relationship I have with my boss by putting him or her in such an uncomfortable position. Making your boss uncomfortable in the promotion discussion is exactly the opposite of what you want.

    The secret to getting promotions is to get your boss on your team – rooting for your success. When I’m working towards a promotion I want my boss to be my biggest cheerleader – I want my promotion to be a day he celebrates with me, not a day where I finally get him to capitulate.

    Turning the promotion conversation into a journey means that you reframe the conversation away from a “yes” or “no” decision and towards a “what will it take for me to get there and how can you help me” conversation – which is almost never met with a “no”. A journey, unlike a binary decision, carries no defined date, which means you’re only asking your boss to join you on a path towards a promotion which you’ll define together. This is fundamentally different from “asking” for a promotion. It turns the promotion into a win-win scenario for both parties. You give your boss the opportunity to define all the criteria and skills he’d like in his ideal candidate and you get absolute clarity and buy in on what it will take for you to get there. This approach might seem like it will take a bit longer but it’s infinitely more effective than forcing an on-the-spot decision.

    Here are four ways to get your boss to join you on your promotion journey and become your biggest cheerleader:

    1. Tell your boss what you want 12 months or more before you actually want it.

    This one may be frustrating for those of you who are dying for that promotion right now, but you need to be patient. The earlier you engage your boss in the promotion journey the sooner it will happen for you, but you just can’t force it.

    2. Engage your boss like a friend and mentor – not like an adversary.

    People respond well to being approached as a mentor. Don’t make the promotion discussion overly formal either, keep it friendly. You want your boss to WANT to help you get there. By not forcing her to make a decision on the spot and by soliciting her help as you work towards your goal, you’ll accomplish that.

    3. Don’t focus on dates – focus on skills, deliverables and development.

    You need to re-frame the promotion conversation to be about you achieving specific development milestones. Maybe you need training or you need to improve on a particularly metric or deliverable. You need to work with your boss to set up a list of achievements that when met will mean you’re ready. This puts you in the driver’s seat and in control of how long it will take to get promoted.

    4. Maintain a regular dialogue to understand your progress towards the goal.

    This doesn't need to be formal – in fact I recommend it isn't. But one way or the other you need to be talking to your boss about your progress at least once every couple of months. Do not let it go for six months or a year and then bring it up again all of a sudden – that’s just making the same mistake all over again. And when you do talk to your boss about it, keep it light, let her know how good you’re doing on your journey but don’t push it too hard.