How to Sell Challenging Ideas

At some point in your career, you will have to convince your colleagues that your idea is the best one. Use this approach to overcome any resistance you encounter.

Written by Paul Rowe
Published on May. 18, 2022
How to Sell Challenging Ideas
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What do you do when you have to sell a challenging idea to your colleagues?

Before beginning, I should note that I consider anything that a stakeholder might fight you on to be a “challenging idea.” At a certain level in software development, you should expect to be challenged on your ideas in almost every scenario. Learn to love this struggle because it doesn’t go away. 

But even when you do love being challenged, it can get frustrating, especially when you’re confident that you know the best way forward. That’s why you have to get good at selling these ideas.

I consider selling a challenging idea to be like playing chess. You need to be tactical, patient and a good sport whether the game goes your way or not. 

But I’m no grandmaster. For every victory I’ve had, there are at least two or three items I’ve struck out on (although, in baseball, that’s a solid average). The reality is that proposals will fail a whole lot of the time, whether because the business doesn’t see the value of the project, you overlooked something important, or even something silly like not having enough buzzwords in your pitch to make it exciting.

Here’s the trend I’ve found: When my ideas have succeeded, that success happened at times when the conversation was rooted in deep, two-sided transparency. By that, I mean one participant is open and honest about the motivations and shortcomings of the idea, and the counterpart is open and honest about the motivations behind their resistance and — importantly — are willing to be convinced. If neither party is open to criticism or change, you aren’t going to get very far.

4 Steps to Sell Challenging Ideas

  1. Prepare the idea.
  2. Sell the dream.
  3. Implement the changes.
  4. Repeat the main points.

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Prepare the Idea

Don’t just toss off your idea in an offhand conversation if you want anyone to seriously consider it. Sure, some ideas will get through with that approach, but it will be much easier to resist your idea if you haven’t prepared yourself to discuss it.

Identify the problem in an obvious way

You want to make the problem you’re solving extremely clear and measurable. You also want to make sure that the stakeholder recognizes the problem and its impact. Ask clarifying questions to get them on board. “Do you understand how this slows down our developers?” or “Do you see why this frustrates our users?” are good, clarifying questions to ask.

Can you simplify your idea?

Simple solutions are easier to understand and plan for, so they win quicker support and ultimately last longer. If your idea is inherently complex, really focus on breaking it down into very simple and small steps.

Are there other options?

Before you meet with resistance, plan for it. Come up with other options that you could consider, including the “do nothing” option. Your idea will always face a competing solution, so carry out your due diligence. You’re almost certainly not the first person who has experienced this problem.


Sell the Dream

Once you’ve prepared your idea, it’s time to sell it. At this point, I’m going to sincerely recommend a bit of light reading: the classic book on persuasion, How To Win Friends And Influence People, which focuses on how to see another person’s point of view in order to achieve your own goals. Some of this section will reference points made in that book, but I won’t attempt to summarize it here and recommend that you read the source material instead.

Use small words and simple illustrations

Light confusion can lead to hard resistance, so you want to make understanding your idea as easy as possible. For example, focus on the overall benefits instead of deep technical dives that are difficult to digest. Make it so easy to understand that it seems simple to implement because your plan is so clear. Avoid anything that isn’t absolutely critical to mention; things like technical jargon, names of tools that only engineers will see, or complex flow charts can all be left out.

Figure out stakeholders personal goals and fears

Think about the selfish desires and fears of the person you’re selling to. What will affect them directly? Maybe they have goals like Management Objectives (MBOs) that would lead to their promotion, or higher Net Promoter Scores that will allow more room for innovation, or better engineering practices that would improve stability while requiring less oversight. Or maybe they have fears like poor maintainability, or they personally lack deep knowledge about the stack. They may simply be worried about whether they want to do any added work. Think about what that individual wants and how you can play into it.

Continually repeat the main value-adds

When pitching, it’s very easy to go down a rabbit hole and forget why you’re even talking about the subject. Keep reminding your audience why you’re discussing this idea and stay focused. For example, restate the core benefits of your idea, like “This is another piece that is going to result in better error messages from our logs, which will decrease our downtime” or “Developers will enjoy this experience more, so they’ll probably stick around longer.”

Be calm and transparent when being challenged

Accept that you will be challenged, even if your pitch is perfect. In this situation, assume that the stakeholder is on your side and is just playing devil’s advocate. Being calm and open to challenges exudes confidence and transparency and may even illuminate things you hadn’t considered that you can now include in your work. Your idea is good (you wouldn’t have brought it here if it wasn’t, right?), so assume you’re already in the planning phase and get ready to call out the potential pitfalls.


They Like It!

You crushed your pitch, and they like your idea … now what?

Don’t just jump right in and start cranking out code. Harvard Business School points out Five Critical Steps in the Change Management Process, each of which clearly articulates your next steps. I’ll paraphrase these steps here, but I recommend diving into the source material if you see this as a potential weak point in your selling process.

Prepare the organization for change

Help employees recognize and understand the need for change by selling the dream to them. This can reduce friction and resistance in the implementation phase as well because the idea will get challenged there, too.

Craft a vision and plan for change

Define the following as clearly and visibly as you can:

  • Goals  The problem you’re solving and the end result you want to achieve. 
  • KPIs  Key performance indicators, which will show you whether you’re succeeding in your mission. 
  • Stakeholders  People who are going to influence the outcome and be affected by the end result.
  • Scope  Strictly defined boundaries of what you will do, what you shouldn’t do, and any flexible areas along the journey.
  • Your “Oh Shit!” plan - What happens if you need to abort the mission for any reason? This is the fallback plan, and the simpler (read: less risky) this is, the more likely people are willing to take the leap with your idea.

Make clear what you’re going to do, who will do it, how you’ll measure success, and what you’ll do if it ultimately goes sideways.

Implement the changes

Follow the steps of your plan closely, but also allow your plan to evolve with any changing conditions along the way. Continually repeat your vision and the benefits of the final result. Empower your team to make decisions and take ownership of the plan along the way. And keep an eye on things so you can anticipate and clear roadblocks for your team.

Embed changes within company culture and practices

Make sure that your new approach sticks and prevent backsliding into “the old way” of doing things.

Review progress and analyze results

Completed does not mean successful. You’re going to now have new problems, new ways of maintaining, and new opportunities to grow. Continue planning your next steps and keep an eye on things as they’re adopted.

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Repeating the Main Points

(Hah, see what I did there?)

Overall, your idea will likely succeed if you are transparent, keep things simple, and continually remind your team of the reasons you are doing something. You will overcome challenges if you cultivate your “sale” for the reasons that matter to the individual. And overall, you want to be a kind and collaborative teammate, no matter the outcome. If you’re a good sport when your idea isn’t accepted, you set a strong foundation for your next idea to gain traction.

At Method, we design, strategize for and build all types of software for our clients. Beyond just delivering a quality product, our duty is to teach our clients practices to leave them stronger as individuals and as an organization. Sometimes this means effecting change in ways that I’ve described here and helping forward-thinking individuals craft their plans for success. You can also reach out to me on LinkedIn or Twitter and follow what we’re up to

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