I WANT A RAISE! How to Get Everything You Want and More From Your Boss.

By: Jeff Hoffman

When I think about tough conversations a rep might have with their boss, three big ones come to mind. From compensation splitting and territory assignments, to the right way to ask for vacation and how to increase your potential earnings. Below you’ll find out how to tackle the most common challenging conversations you’ll face as a sales rep, all while keeping your reputation and earnings intact.

Here are the top three most common conversations in order of difficulty to obtain and how to get what you want from them.

1. Compensation on a shared deal

Here’s the situation. You’re the rep covering the NYC territory, and your colleague is covering Chicago. The rep covering Chicago recently closed a deal in their territory, but you discover it’s a subsidiary of one of your NYC accounts. The Chicago rep wants to get paid, but so do you, because it’s your account. So, you both decide to approach your boss/manager and ask for double comp on the deal.


This is NOT a fight you EVER want to take to your boss. Attempts to bring management into compensation issues when arguing on territory assignments or ownership are FUTILE. This is the lowest level of conversation a manager wants to engage with.

Why? Because even if you end up winning this round, you will lose later. No compensation or commission is ever worth you saying to your company, ‘I want the company to pay twice for this one activity.’

The real conversation must be handled by the reps themselves. Work it out between you and the Chicago rep. Decide on what makes sense for you both, and then move on. This is one tough conversation that you definitely do NOT want to bring to your manager’s attention. You will tarnish your reputation as a hardworking rep, and look like a fool in front of your boss, the finance team, and your company’s leadership.

2. You want to take time off

And when you want to take time off, you really want to shut down. No emails, no phone calls, no juggling your pipeline from the side of the pool in sunny, warm California. You really don’t want to be bothered at all; you want to enjoy your time off and really unplug and recharge.

The problem here is that your boss has expectations that even on holiday, his reps are available. The good news here is that this is one you can win. Here’s what to do.

Two months before your planned vacation, enlist the help of a colleague and ask them to be an administrator for your deals for the week that you’re gone. (Of course, this comes with the promise that you will do the same for them while they are gone.)

They don’t have to be proactive with your accounts, but they do have to be the last stop if any of your prospects try to reach you. (Read: it should never get to the point where your prospects are contacting your boss!) You do NOT want your boss to do anything. You want to ensure that you have your work covered, and it will be like nothing has changed while you are away.

One month before your planned vacation, proactively call and contact any deals in your pipeline. Inform them of the days you will away and unreachable, and that while you are on vacation your colleague will be taking calls and answering your emails, but nothing significant will happen until you return. This could also help you move some deals through quicker, which is a huge plus going into this conversation with your boss.

Both of these conversations have to happen BEFORE you even think about going to speak with your boss. Once you’ve done both of these items, schedule time with your boss, and bring the colleague who will be assisting you with you to the meeting. Report on steps 1 and 2. Your conversation should go something like this –

‘I am taking a vacation on these days (x – y) and I do not plan on checking in, as I really want to recharge and unplug. It’s not for another month, and I have already recruited Bob, here, to help with my accounts. I’ve also spoken to all of my big deals in my pipeline and informed them of my time away. My question to you, boss, is what else do I have to do so that I can truly check out and be that much more energized when I come back?’

The important point here is that you never want to be a problem for your boss, you want to offer a solution. If you want to take time off and truly unplug, take the time to set yourself, and your company up for success before approaching your boss with this huge request.

3. I want a raise

This conversation is not as impossible as the double comp request, however it is not guaranteed like vacations. It requires skill, and a bit of luck.

If you want to approach your boss with this, keep in mind  that you ALWAYS want to negotiate for more opportunity and/or better accelerators. What does that mean?

If you look at a comp plan from left to right it shows your full earning potential for the year. The numbers on the right are always the highest, and reflect your max earning should you exceed your quota. Your conversation around compensation should always be to the right of your comp plan.

Things that are okay to ask for in your salary negotiation:

‘If I am over 100% every deal gets an additional commission bonus of x%.’

‘If I am at 150% of my goal by the end of the year, I want to make $180k, not $150k.’

Both of those are acceptable negotiations to have with your boss. For success in this conversation with your boss, you always, always want to negotiate for additional commission and/or bonus for exceeding your quota.

Things that are NOT okay to ask for in your salary negotiation:

‘I want my base salary to be higher.’

‘I want to increase my earnings from $100k to $120k for reaching my quota.’

You don’t want to negotiate a higher percentage of earnings under or at quota. A sales rep is a cog in the bigger picture of your company; a cost of goods sold that your CEO has already factored into selling your product. If you negotiate for the over-goal percentage, it’s easier for your company to pre-approve a higher accelerator because it doesn’t show up on any part of their plan. What that means is, they have planned to hit quota, and anything over that is a much better pitch to your manager, and executive team.

Another thing to consider is rather than negotiating salary and payout, negotiate for more opportunity! Now, more opportunity is not the same as better opportunity. If you say that you want NYC because it is a better territory, it doesn’t necessarily mean that you’ll get it. I’d recommend asking for an expansion on your current territory, or selecting a few opportunities in an under-pursued industry. You might be interested in medical device companies, and what your product can do for that industry. Make it easy for your manager by showing your commitment to overachieving and desire to put in the work for your company’s success.

Overall, you always want to be the rep who does things that solves your manager’s problems. Asking for double comp, or a base salary raise does not help your manager. When you want something from your manager, you want to make it as easy as possible for them to give you want you want. Be empathetic to your manager.

Show up to the door of your manager’s office with a solution. The ‘I’ve got a problem can you help me’ is a bad approach with managers. However, the ‘I’ve got a problem and this is how I’m managing it,’ speaks volumes to your manager. Only offer your boss additional solutions, not additional problems.

What’s the toughest conversation you’ve had with your boss? Managers, what do your reps do that make you grant their requests?

Stay in the loop.

HOFFMAN is an innovator and sales visionary. They deliver an authentic experience that keeps sales people engaged.”

- Bret Wilbur, Director of Sales, TriNet

Let’s get

  • This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
  • This field is for validation purposes and should be left unchanged.