Have an Idea? Here’s How to Sell It to Your Boss.

Know your audience and avoid messy messaging to get your ideas across.

Written by Vanessa Gennarelli
Published on Sep. 12, 2023
Have an Idea? Here’s How to Sell It to Your Boss.
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I invite you into a common work scenario. Your team is considering changing from an old system to a new one. Whether it’s a customer-relationship management system, project management software, observability tooling or a new language or framework, we’ve all had to face this problem.

You’ve likely seen two archetypes:

The Super Communicator. This person moves through the organization with ease. The organization fast-tracks her promotions, she lands the most interesting projects and leaders pick up and use her turns of phrase. 

The Idealogue. This person has a strong point of view that they righteously carry. They frequently come out of meetings feeling frustrated and ignored. 

Both individuals are smart, competent and possess enviable expertise. The key difference is that the Super Communicator knows how to sell her ideas and the Idealogue doesn’t. 

3 Tips for Pitching Your Ideas at Work

  1. Analyze your audience. Find out the professional background, goals, and values of your decision-maker.
  2. Package the value. Showcase the impact you expect to see, making the choice a no-brainer.
  3. Surface trade-offs. Consider other options with their downsides, and underscore the ramifications if people don’t implement your idea.

The notion of selling might not sit well with you. Fifteen years ago, it sure didn’t for me. I’d read job descriptions that included words like influence, persuasion and clout and would instantly feel icky. You can think of these strategies as managing up, but I prefer to think of them as relating to the organization — articulating what you want in a way the organization can hear you.

And the stakes are high: if you don’t learn how to sell your ideas, you’ll limit your reach. Ideas and initiatives that succeed have momentum. That means others need to buy in to your idea and make it their own. For your ideas to resonate with your boss, VP or CEO, you need to know what matters to them.

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Audience Analysis 

I ask direct reports to think through the following questions about their audience:

  • What’s their background?
  • What motivates them?
  • What are the success metrics for their roles?

Study the audience’s background

First, find out about the arc of their career. LinkedIn is your friend here. See if you can detect patterns in terms of the size of their previous organizations, areas of focus or consistent themes in their work history. 

If their work is varied, they might be a generalist. If it’s specialized, you may need to find out more about the domain that matters to them. Then you can use the data in two important ways.


Tailor your message

Use their background to connect their understanding of the world to your idea. Finding comparisons relevant to their background is always helpful. A colleague of mine worked at NASA, so when we were talking about launching products, we used preflight checklists to ensure consistency. For computer science teachers, we’d relate Git to the data structure of a linked list, something they would recognize.


Infer the impact it wants to make

If your audience is a product person, they might want to grow the organization through features and technology. Or perhaps they are more of a sales-driven leader, focused on maximizing and extracting value out of a mature offering.

This approach applies both to working with other teams in the organization and to collaborating with peers. When you understand your negotiation partner, your chances of success increase by orders of magnitude.


Consider how they get evaluated

What are your audience’s incentives? Which numbers does the company expect this person to move? If you’re not sure, take a look at their team’s key performance indicators, their dashboards, even job descriptions on your company’s career site. If your company is mature enough to have career ladders, that’s another great source of intelligence about how this person gets measured by the company.

Surviving Change at Work book jacketIf you’re unsure about your audience’s goals, their place in the organizational chart will have some info. Line managers often have more operational goals, like feature-level metrics, shipping on schedule and conversion rates. People higher up in the organization have broader goals, like revenue and activation metrics, gross margin for the company and expansion into new verticals.

Remember to keep your audience’s place in the organization in mind. I’ve seen a few presentations fall flat because the presenter was caught up in the weeds of features while pitching to leaders with business-level goals.

Once you have a sense of how they are measured, refer to that goal in your messaging. You’re more likely to succeed if you can frame your idea in terms of meeting a joint goal.

Here are a few conversation starters you can use to brainstorm:

  • “This will help us both meet a higher margin by... ”
  • “I saw that you’re also looking to lower your turn-
    around time... ”
  • “This initiative will meet 27 percent of the company’s
    growth goals.”

Suss out their priorities

If you’re not sure about a leader’s priorities, speak to goals surrounding progress and excellence. These are big motivators. For example:

  • For a leader who is motivated by progress, describe what you need to work five or ten times faster.
  • For a leader who is motivated by excellence, describe how you can increase customer satisfaction or market dominance.
  • If you’re still not sure about your audience’s background, goals, or priorities, listen to the words and phrases they repeat. Consider using those words in your own messaging.

Now let’s take what we’ve gathered — the priorities, the common turns of phrase, the metaphors that will speak to a leader’s background — and turn to the output: crafting a successful message.

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Packaging the Value 

In my experience, leadership meetings have two core activities: weighing proposed solutions and making decisions. Your company has hired smart people, and those smart people make the case that we should focus on performance, or growth, or market share, depending on their role. How do you make your idea stand out from the rest? How do you present your idea in a way that makes it easy for leadership to say yes?

Here’s how:  Use the Pain, Dream, Fix framework to make your storytelling airtight.

Decision-makers don’t have a lot of time, so don’t waste it with a messy message. A few common messy-message offenders:

  • Navel-gazing. When you start with “Today, we're excited to announce” or “We are thrilled to introduce” or “I’m excited to show off,” that messaging makes the idea about you. It’s great that you’re excited, but why should the audience care?
  • Going too deep. Experts who are really close to a project can use way too much detail. They care so much about the project that their pitch becomes about them rather than the project’s value to the organization. Keep your message short and high-level. You can always dig deeper if you get questions.
  • Being too vague. Phrases like “we’ll make something great,” “Modern tooling, the way it should be,” “Launch something amazing,” have all the tangibility of vapor. What is the decision maker saying “yes” or “no” to, exactly? Show them a clear problem and a concrete solution.

To boil down messy messaging into quick, clear points, I use the Pain, Dream, Fix framework I learned from business leaders and educators Alex Hillman and Amy HoyPain, Dream, Fix looks at three anchor points for your messaging:

  • Pain: Describe the problem in a way that homes in on the pain your customer, audience, or company experiences.
  • Dream: Next, narrate what the same situation would look like if you dissolved that pain. Would it be easier, faster, smoother?
  • Fix: Once your audience is primed and in that problem space with you, introduce your proposal. It could be a product, a service, or an idea.

Once you can spot Pain, Dream, Fix in the wild, you’ll see it everywhere, especially in infomercials, commercials and ads. 

Next, let’s apply Pain, Dream, Fix to a few work scenarios. You probably hear “messy messaging” all the time — going too deep, navel-gazing, and being too vague are all examples of asks that don’t clearly package value.

Since the audience here consists of decision-makers, focus on the pain the company feels (not you) in quantitative terms of time, capability, and capital. Then describe what the results of your proposal will look like, and their impact. 

Finally, usher in your solution as an obvious solution. It’s a recipe for an airtight message that’s easy to parse.

Excerpted with permission from Surviving Change at Work by Vanessa Gennarelli. Published by A Book Apart, September 2023. 

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