You need 3 greenlights, not one

Most people think their boss wants a polished plan served on a silver platter. For good bosses, that’s not true – we want to see some of the dirty work.

👋 Hi, it’s Greg and Taylor. Welcome to our newsletter on everything you wish your CEO told you about how to get ahead.

It happens all the time – I ask someone to evaluate an opportunity or solve a problem and they return three weeks later with a polished plan, expecting my rubber stamp of approval.

20% of the time that works, but 80% of the time it ends in frustration for both of us. Either we’re not aligned on the scope or objective, their inputs or analysis seems incomplete, their recommendation is too safe or too delusional, or the problem/opportunity is no longer a priority. 

When this happens, I start asking lots of questions, brainstorming new options, and basically hijack the discussion. I’m frustrated and they’re frustrated – they did a bunch of work and I'm pulling us back to the beginning. 

Most people think they should present a final solution. But the more senior you get, the more complex the problems you work on become. There usually isn’t an obvious right answer. So you need to work differently to get your boss on board. You have to get buy-in along the way. 

This feels risky/vulnerable, because it means showing your boss unfinished work. But the reality is that as a CEO, I love working with people who do this well. I have more confidence in the decisions we get to, and they become my go-to people. 

So here’s our playbook for getting buy-in along the way, and avoiding frustration for you and your boss.

– Greg

Your 3 greenlight moments

As you get more senior, investigating an opportunity or solving a problem becomes more complex and more high stakes. Often there’s more than one (or no) good solution. Here are some examples of this type of decision: 

• Deciding the company’s product roadmap

• Evaluating a new GTM plan

• Selecting a new market or vertical to enter

• Building a plan to increase NDR/renewal rates

• Finding cost savings of X%

When tasked with a challenge like this, most people’s instinct is to go away for a few weeks, do a bunch of research and work, and return with a final solution ready for a greenlight. They expect a few questions and approval (or not).

But this rarely works, because rarely does all the data and evidence line up perfectly to point to one clear path forward. Usually, the decision is a mix of analysis and business judgment – which means your boss wants to see your inputs and other options you considered. This is why these presentations often devolve into brainstorming or a request to “go back to the drawing board.” 

Instead, run a process that gives your boss multiple greenlight moments. This helps you get your boss’s buy-in along the way, avoid the meeting hijack, and know you’re already 80% aligned at the final greenlight moment.

Here are the three moments for greenlight/buy-in, and the deliverable that corresponds with each.

1. Objective Greenlight (via a Project Brief)

In this phase, you’re making sure you and your boss are aligned on the scope of the project.

The initial mandate to work on a project like this often comes in a meeting or via Slack message. Create a project brief (a working document) where you lay out the project background, objectives, scope, and any initial data.

Do this fast, preferably within 2 business days of the initial ask. Then tag your boss in the document, tell them you want to make sure you’re aligned, and ask for their feedback, edits, and confirmation.

Make sure to include:

• The specific problem or opportunity you’re addressing

• The goal/what you’re optimizing for (i.e. “find a new vertical that can generate $1M in revenue next year” or “reduce vendor costs by 10%”)

• The scope of the project including time frame and budget – if this wasn’t included in their initial ask, you should suggest these parameters for them to react to

• Priority/urgency of the project – when the decision is needed and its urgency relative to other projects

Also, let the boss know that if they don’t respond by a certain date, you will move forward – since you are looking for alignment, not approval. 

For example, here’s what an initial Slack from your boss might look like: 

Your project brief should be short but specific, making sure both you and the boss are aligned on the scope of this assignment. Here’s how you might respond:

2. V1 Plan Greenlight (via a Project Plan)

In this phase, you’re making sure that you and your boss agree on your plan for how you’ll tackle the assignment.

Within a day of your boss’s first greenlight, add a V1 project plan to your project memo (yes, that fast – work late if you need to). Your plan isn’t the proposed solution, it’s just your roadmap for how you’ll decide on a solution.

It should include:

• The inputs you’ll gather to make a decision (customer data, competitive analysis, interviews, etc.)

• The resources you’ll need to do this (including from other teams)

• Your timeline and key milestones

• A committed date for first review

Share this with your boss and any other close stakeholders for feedback – for example, if you’re evaluating a new product line, share the plan with the head of sales, head of product, and head of operations. You’ll likely need their input and alignment on this project as well.

Tell stakeholders to leave suggestions and any questions, and ask your boss if they’re aligned on this plan (and to suggest any changes). Leave comments open so others can see the full conversation.

For example, in the NDR scenario, my project plan might look like this:

3. Plan Options Greenlight (via Working Session)

20% of the time, all your research and data will point to a clear correct solution. But usually, this isn’t the case – there are 2-3 potential paths forward, and it’s a judgment call. Once you’ve built out these options, it’s another good moment to get your boss’s feedback.

Use a working session (45-90 min depending on the topic) to explore each option and build out the upsides/downsides of each. In the session, you might end up eliminating one or more of the options, or adding 1-2 new options to the table.

Your goal is to 1) get your boss up to speed on the same data you have and 2) give them a chance to explore alternatives (including the pros and cons) before the final greenlight moment.

Start the session with 1-2 slides that get your boss up to speed on the situation. This should include:

• A reminder of the objectives, goals, and what you’re optimizing for

• The analysis/evidence you’ve accrued to date

• A simple slide with a description of the options and a few pros/cons

Send this as a pre-read and then review the slides in the first five minutes of the meeting. After that, explicitly tell them that you want to hear their initial reaction / feedback. Execs are usually either absorbing information or problem solving – you should clearly indicate to them when you want them to switch into problem solving mode.

Be open to tangents and new options added to the table. You’ll likely leave this meeting with more work to do (something new to explore, or a different analysis to do). But better now then after you’ve already completed your recommended plan.

End the working session by summarizing next steps and any options added or removed from consideration. Once in a while, if you’ve uncovered multiple new options or changed the scope of the project, suggest scheduling another working session.

But spend 10% of time getting your boss up to speed, 80% of time exploring options, and 10% of time on next steps. Great working sessions are high value and time efficient. 

Rough carpentry vs finished cabinetry

It’s vulnerable to show your boss a plan that isn’t fleshed out or admit you don’t know the right path forward. But most bosses don’t want to just rubber stamp things for approval – especially decisions that are high stakes or complex. 

If they’re a good boss, they got there because they’re good at solving problems and understand that it’s a messy, complex process. So you can actually build confidence (not deteriorate it) by showing the creation process (rough carpentry) rather than just the end result (finished cabinetry).

There are multiple benefits to working this way:

• Less last minute feedback that feels out of nowhere and results in extra work

• Less wasted time from building out a solution that isn’t implemented or working on a problem that’s no longer a priority

• Stronger plans/decisions because they leverage your boss’s expertise and experience

• Less personal risk for you – if the solution fails, you had your boss’s buy-in earlier

• Faster buy-in from your boss, since they contributed to the solution

Our advice

Executives are often evaluating your process as much as the outcome, because it shows us how you work, collaborate, and think strategically – even if the project doesn’t work out. 

It’s scary to share unfinished work, but it’s also a great way to build trust and confidence with your boss, especially if you haven’t worked with them before. Running this process teaches you how your boss approaches problems and teaches them to trust your process, since inevitably not every decision you make will be the right one.

And if your boss doesn’t like to work this way, or is too busy to do so, run this process with a proxy. Find another person on the team whose judgment your boss trusts, and ask them for their thoughts at each of these three steps. Use them to pressure test your plan and signal credibility.

However you do it, the advice is the same: Don’t build everything for one greenlight moment – create multiple greenlight moments throughout the process, and avoid a meeting hijack and wasted work. 

To the next 10 years,
Greg and Taylor

P.S. If you have other suggestions for how to do this well – share in the comments.