Boss Won’t Help You Prioritize? Ask Madeleine

Dear Madeleine,

I am an EVP of sales in an organization that is growing insanely fast. I have a brand new Chief Sales Officer and my regional counterpart just quit—so I have gone from four direct reports leading 300 people to seven direct reports leading 700 people.

I would have thought my number one job would be to make sure everyone is on track with their quotas—but, as it turns out, no. I mean yes, but in addition to my new boss being hell-bent on my getting everyone to quota, I have to complete 27 projects. I am not kidding. I sat down over the weekend to create thumbnail project plans for each project and there are literally 27.

I tried to talk her out of my needing to complete all 27, and to get her to prioritize them—you know, the 80/20 rule—but she just waved her hand and said: “You are such a rock star; I know you will figure this out.”

I am so overwhelmed, I don’t even know where to start. Everyone is barely keeping up as it is because there has been so much change in the organization. I can’t even begin to imagine how we are going to get everything done.

Any thoughts will be appreciated. I think …

My Boss is Nuts


Dear My Boss is Nuts,

Well, she might be. Or, more likely, she is just very green. She is making the classic rookie error of so many who want to make a splash when they hit the C-Suite: too much, too soon, too fast.

If your new CSO is like any other in a fast-growing organization, she is probably being driven by a relentless CEO who is being driven by an uncompromising board and very vocal investors or shareholders. She hasn’t figured out how to discern between what really matters to her CEO and Board and what is just an idea—so she is just going to pile it on you. It is the senior leader equivalent of throwing spaghetti at a wall to see what sticks. It is a terrible strategy, but a lot more common than you’d think.

So it is up to you to figure out what matters most and what is actually doable. The first thing to do is create a matrix of all the projects and organize them by:

  1. the ones that will make the biggest impact on revenue generation; and
  2. the level of difficulty.

Since hitting or exceeding quota is job number one, prioritize everything that will help everyone to do that. Start with the least complicated and get a toehold on the more complex, longer term ones.

Everything else can get slotted into the calendar after these get going. You may or may not ever get to them—but if you are crushing the numbers and most important projects, it won’t matter that much. Then the projects that are still important will bubble to the top and the rest will just fade away.

Don’t forget that you have seven VPs, they all presumably have multiple directors, and you actually have 700 human beings to deploy to make this all happen. That is a lot of manpower available to you. Last time I checked, sales people tend to be very motivated by bonuses.

So sit down with your seven VPs and think this through. Spread the work. Be creative. Be clear about outcomes. Create timelines. Share them with your boss and invite feedback. You probably won’t get much—she obviously trusts your judgement.

You probably can’t get everything done, but you can absolutely get the most important things done.

Trust that your boss trusts you and that you will absolutely figure it out. Breathe, keep your wits about you, and rock on.

Love, Madeleine

About Madeleine

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response soon. Please be advised that although she will do her best, Madeleine cannot respond to each letter personally. Letters will be edited for clarity and length.

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