Asking Better, Getting More: The Basics

Early in my career I got a great piece of advice: getting good at anything is like training to fly a plane. You need to clock a certain number of flying hours to get from First Officer to Captain.

Here’s the problem: often when it comes time for women to ask big or negotiate they just haven’t put in the flying hours. That makes asking for that raise or promotion feel even more nerve wracking.

While these conversations can be hard, there’s no need to assume the brace position: you are not going to crash and burn. Nearly a decade into my sales career and tens of millions of dollars later, I’ve put in the flying hours for you--including a few botched takeoffs and rough landings.

Here are my 5 hacks to act like a Captain and successfully land that plane at your desired destination.

  1. Come prepared. There is little that is more powerful than coming prepared. No matter what the circumstance is, this is a tough-conversations-life-hack. It’s so easy to do your homework and it can make-or-break the effectiveness of your ask. Preparation is the difference between making a principled ask that your boss can thoughtfully consider vs. having a live brainstorming session for a half-baked idea that gets no traction. Here are a few prep tips, depending on the circumstance:

    • If you’re going for a promotion, are you ready to speak to your accomplishments and--very importantly--how they have directly advanced the organization’s goals?

    • If you are negotiating for a raise, come knowing what you are specifically asking for, why you’ve earned it (same as above), and why you’re asking for that specific increase at this time. Also, have you checked Glassdoor to see what others on your team are being paid or what others with similar roles at your competitors are being paid?  

    • If you’re asking to go to a conference, have you researched the cost of the flight, hotel, and daily expenses, not just the registration fee? Can you articulate why this is good for the organization and not just exciting for you?

    • If you’re planning your maternity leave, have you checked the company handbook to confirm the policy? Have you done additional research on how that stacks up to what your competitors offer or how others in your organization have structured their leave?

  2. Be formal. Here’s an important rule: whenever you ask for something, keep in mind you are having a formal business conversation. Be authentically “you” but give the conversation the gravitas it deserves. That’s why hack #1 of coming prepared is so essential.

    That also means finding dedicated time to have the conversation in a private place and not in an open work space or at the coffee machine. Don’t ask to grab five minutes in between meetings. Rather, send an invitation to hold time or wait until your regular check-in with your manager. Also, send an agenda with that invitation outlining what you plan to discuss. Nobody wins when your boss is caught off-guard. This gives your boss a chance to collect their thoughts in advance or check budgets. Remember, it’s your job to come prepared. If you enable your boss to come prepared too, then you are really building the framework for a productive conversation.

  3. Lead with confidence. This is often the hardest part. Any conversation where you are asking for something (be it a raise, a promotion, or even some extra vacation time) can be stressful. For many of the women I work with, these types of conversations are a once or twice a year occurrence so the stakes feel really high and the practice rounds feel really low. Naturally, it can be difficult to feel confident and even harder to project that confidence. This is often evident when I role play with my clients or I review a written proposal they are submitting. I frequently see three phrases I absolutely, positively HATE: I hope….I think…. I believe.

    So here’s a speaking-with-confidence-life-hack:

    Eliminate those three verbs from your vocabulary and replace with “I suggest” or “I propose.” You will instantaneously project confidence and, per hack #2, also reinforce the formality your ask deserves.

  4. Establish next steps and document them. This is a rule I learned in sales: you never (ever!) leave the conversation without formalizing next steps. So how does that translate to making an ask of your boss or perhaps a future boss if you’re negotiating a salary for a new job?

    Simple.  Only rarely is your boss going to have an answer on the spot. In fact, I’d argue that if you get “yes” right away, you didn’t ask big enough.

    Make sure you leave that conversation with mutually-agreed-upon next steps, including a timeline for when you can expect an answer or at least a status update. Also, document your conversation so that you both have a record of the “what” and “why” of your ask.

    So how do you put this all together? Easy. Send an email on the same business day of the conversation, including these key elements:

    • Thank them for their time and for considering your ask.

    • Overview what you discussed.

    • Reconfirm that you will follow up with them at the mutually-agreed-upon date if you haven’t heard back and… this part is really (really) important...

    • End with a question such as “is this in sync with everything you took away from our conversation and did I miss anything?” This should prompt a response back affirming that you are on the same page. Confirming you are on the same page is absolutely critical: how can you expect to achieve your desired outcome if you and your boss don’t even agree on what that desired outcome is?

  5. Follow up. Seriously, please follow up. You put so much work into having this conversation and you owe it to yourself to see it through. Too often, after women have expended the energy to prepare for that big conversation and expended their capital in making the ask, they are too shy about following up. Do not undermine yourself by letting the conversation go unfinished. Remember from hack #2: this is a formal, business conversation. Remember from hack #4: you agreed on next steps, including this checkpoint.  If the mutually agreed upon time (i.e. the end of the month) comes and goes without resolution, give it a one-business-day buffer. After that buffer, it is your responsibility to follow up.

    …. Still feeling nervous or shy? Consider this: your boss might even be waiting to see if you follow up to evaluate how serious you are.

Asking Better, Getting More is a recurring blog series for Something Major Coaching dedicated to better negotiations and making tough conversations easier. Have a question on this topic that you want me to answer or want to set up a session to work through your big ask? Shoot me an email: or get connected via social, below.