How to Turn Your Boss into Your #1 Fan and Advance Your Sales Career

The standing joke in Denver, Colorado, is if you don’t like the weather, wait a few hours. Sometimes sales reps feel the same way about their bosses.

The truth is, sometimes you’ll get a great boss, and sometimes you’ll get Mr. Hyde. But no matter your opinion of your boss, you’ll need to move the relationship forward if you want to advance your career.

Let’s start by outlining the pure power your sales manager has to make life a little easier for you:

• Recommends you for a raise and promotion
• Distributes a bluebird to someone who can handle it (YOU, of course)
• Becomes a KEY reference for any future job changes
• Approves that two-week European vacation you want to take
• Recognizes you publicly and promotes you to the higher-ups

Now let’s look at what a strong leader can choose to do for you:

• Show you your blind spots
• Help you close impossible deals
• Advance your current skills
• Promote you and give you political shelter
• Fight for your commissions
• Give you a generous territory

Now that we’ve covered the power and influence your boss has over your career, you can see why building a positive relationship is worth the effort.

Eleven Simple Steps to Turn Your Boss Into Your #1 Fan

No one will manage your sales career for you, so if it’s to be, it’s up to you! The following steps are practical, actionable, and worth your consideration.

#1. Show your appreciation for your boss’s time, effort, and resources. This can be done in several ways, so here’s an actionable example. One salesperson we know gave a shoutout on LinkedIn to their boss. It was a simple visual post that said “Amazing Sales Leader” and read, “Mike, appreciate all you do for our team.”

#2. Always keep your boss in the loop. If you lost a deal on Monday, don’t tell them Friday. Let them know ASAP. Share it all, the whole enchilada, not just the wins. Be quick with disclosing the losses, because the longer you wait, the worse it will be.

#3. Make yourself readily available. Be there for the meetings and calls, because there’s nothing worse than calling someone who never picks up. 

One of my clients had someone on the team who never answered the phone. Every time she called, she got the rep’s voicemail, and sometimes the rep took hours to get back to her. That’s not the behavior path to promotion. 

Unless you are ALWAYS on your phone closing deals or prospecting, answer your boss’s calls.

#4. Speak up instead of staying quiet. Don’t be afraid to have an opinion and voice your concerns or ideas candidly. Approached correctly, this can lead to increased responsibility within the organization. 

Just use good judgment: speaking up doesn’t have to mean complaining. Speaking up can mean “here are some problems, here are some ideas to solve them, how can I help?” Complaining, as good as it can feel, never accomplishes anything until action is taken.

#5. Work on the relationship. A strong relationship is built step by step, and one of its critical foundations is respect. Part of your job is to help your boss look good in public. Never forget that. You are like Vidal Sassoon: if your boss doesn’t look good, you don’t look good.

#6. Stay up to date. Know company news and events so you can give thoughtful feedback when needed. At one of our clients, there was a sales leader we’ll call Frank. Frank knew everything going on at the company. 

He knew when the benefits changed, he knew the comp plan in detail, he knew the marketing team, he knew the CEO’s dog’s name, and he even managed to build a relationship with dull Bob in accounting. 

He talked to other employees, built relationships with everyone on his team, read the company blog, and led the revolution against siloed corporations. When Frank’s boss needed to know something, guess who he called first? When Frank’s boss was promoted, guess who got the job? Frank became invaluable.

#7. Understand your boss’s pet peeves. We had a high-level search we needed to get right. The hiring manager reported to a NEW CEO and needed to make a solid first impression. As we interviewed her about the new hire profile, we asked about her pet peeves, because the last thing we wanted was to put someone in this visible role and have them fail over something “minor.” 

It wasn’t a question we usually asked at the time, but she knew precisely what annoyed her, with little thought, and it saved us during the recruiting process. 

We found the perfect person, who had the skills to do the job and cared about building a solid relationship with her new boss, and it became straightforward for our new hire to avoid the irritations and build a strong working relationship quickly.

#8. Embrace your boss’s communication style. Some bosses want email; others want to text or jump on a video call. Some will call your cell and expect a fast response. Whatever their preferred method, adapt. It makes you more versatile across all communication mediums, so if they prefer a method you hate, learn to adapt anyway.

#9. Hold yourself accountable and take the initiative. Building a successful relationship with your boss is essential for both of you. Trust is built by being honest and putting in the effort, and working together becomes much more manageable. 

Keep track of your progress so you can see the fruits of your labor: a spreadsheet of your deals, calls, activities, and daily schedule, whatever you need to stay on target and chip away at your goals.

Don’t Wait Around for Anything

Take the initiative and start making things happen! This makes you more visible and wins over the hearts of those above you on the corporate ladder.

Sometimes taking the initiative will get you in trouble. But I say take calculated risks, and if it’s worth it, do it anyway. For example, in my former life, I started asking around at my huge employer for the list of the TOP 100 accounts. 

These accounts were worth mega millions to my employer, but to me they were worth nothing, because my division wasn’t getting a single dollar from them. My goal was to get the list, figure out how to use it, and start making money for my division.

So I started asking around. I asked and got shut down, and shut down, until one day my phone rang, and it was the head of another division that owned these accounts. I was told to mind my business, and that my boss, the President, would be getting a phone call.

At the time, I was mad. I was trying to make money for the same company, so I didn’t see why this was a big deal. 

But my boss didn’t get upset with me. I think he wanted the list too, but felt it would be less intrusive if I asked for it.

Liberate Your Inner Tiger

So my point is, don’t be the caged tiger. Be the tiger who sometimes gets put back in the cage. You’ll get to your goal much faster. And be willing to risk getting in a bit of trouble. It’s better than sitting around waiting for something to happen.

#10. Be on time. Sounds silly, right? Being “punctual.” If you think you’re above this rudimentary tip, you probably aren’t. Everyone is sometimes NOT punctual, and some people have limited their incomes, career mobility, and reputations by their inability to show up on time. Don’t let that be you. How many deals have you lost by being late?

One for me comes to mind. I had moved to a new home, was still finding my way around, and I’m not directionally gifted to begin with. 

I scheduled a meeting in an unfamiliar part of the Bay Area and drove to visit a company president about recruiting for an opening. I got lost on the way and wound up an hour and a half late. 

The trip took me three hours because of one wrong turn. And don’t worry, this was before GPS and Blackberries, so although you may be able to “understand” why I was late, it was nowhere near acceptable.

Unsurprisingly, I did not get his business. But I did go in and apologize. I let him know why I was late, gave him plenty of free strategic advice, and walked out swearing I’d never let that happen again. This true story embarrasses me to this day.

Being on time all the time is hard. Don’t lose business over it, and don’t ruffle your boss’s feathers.

#11. Keep your attitude golden. I’ve read research saying your attitude is like a set point. Some people are naturally more optimistic than others. 

For the rest of us, it’s daily maintenance. Sometimes all that’s needed is a nap or a conversation with a trusted colleague, but if you find your attitude going south, figure out what works best for you and use your tools to lighten your mood. I can promise you that the reps with the best attitudes make more money. 

They get promoted faster, and their bosses favor them. So work on your attitude, and your sales career will skyrocket.

Getting Ahead Requires Patience and Hard Work

It’s no secret that building a great relationship with your boss can help you get ahead. And if you’ve worked all eleven steps and the relationship still can’t be saved, that tells you something too. Here’s how to know when it’s time to leave your sales job.

If you want to accelerate your career and feel like your current options are limited, get in touch: [email protected].