Managing expectations without looking unambitious

When the boss wants to shoot for the moon, don’t be the skeptic or the kool-aid drinker. Be the honest broker.

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

As CEO, I'm constantly thinking about how to achieve step change improvements in the business (product, growth, or margins). So it’s not uncommon for me to throw out ideas that, admittedly, probably sound a little crazy (shocker).

For example, one idea I’ve shared recently is giving away 100,000 AI crash courses (currently our most popular course) from Section to college students entering the workforce. I think it’s nuts that college kids are being told to “stop cheating with AI” but the moment they enter the workforce, they will be expected to be AI proficient. So if we can help 100,000 grads get a faster start in their first job out of college – how amazing would that be? Plus, it’s a way to accelerate Section’s brand recognition and position us as leaders in AI upskilling (e.g. drive growth).

What my team hears is a need to multiply the current workload that it takes to run one crash course a month (with ~250 students) by 40-50X in a single year. Plus I’ve outlined no clear ROI or business model. So, of course, their reactions range from skepticism to confusion to speculating about my micro-dosing regimen. 

However, when I pitch these ideas, I’m not saying we need to go do it tomorrow. Instead, I usually have an underlying assumption behind the idea (that sometimes I need to be reminded to articulate) and I want the team to engage with the idea and come back with their own analysis. They still might tell me I’m out of my mind, but at least they’ll have thought about it – and maybe (probably) come back with a better plan.

We want team members that can find a middle ground between seeming unambitious or a naysayer and being easily co-opted to support the latest “big idea”. So here’s your playbook for pushing back on ideas that seem unrealistic without looking like you’re playing it too safe.

– Greg

P.S. We’re running a private 1-hour workshop on using AI as a thought partner tomorrow, October 17, from 5-6 p.m. ET. It’s for Personal Math subscribers and friends, so feel free to forward to friends and family. Sign up here.

How to engage with big ideas

We’ve all gotten a seemingly random Slack or email from our boss or CEO with an idea that seems totally out of touch with reality. If you’re lucky, the CEO or exec will give you a bit of context about where the idea is coming from. But usually it looks more like this: 

• Could we reduce headcount by 25% using AI?

• Could we grow NDR 50% next year without growing the CS team by using AI?

• Can we cut vendor/SaaS costs by 20% in the 2025 budget?

• Let’s launch [X] product by next quarter just like [Y competitor] has.

Most of us react to these types of ideas by ignoring them or waiting for someone else to run with it. It’s easy to look at the scale of the idea and roll your eyes – the exec is delusional, has no idea how hard it is to do what we currently do, and has probably just read “Amp it Up” or some other Silicon Valley playbook. As the operator, it’s often stressful to even consider these large ideas, especially if you think you’ll be on the hook for delivering with your current team and resources (a common assumption).

However, two things are typically unsaid:

1. There’s a business objective driving your boss’s idea. It could be revenue growth, better margins, increased brand awareness, or sometimes a mandate from the board (i.e. “all our other portfolio companies are reducing costs with AI”).

2. They’re assuming a breakthrough or a change in the way things are currently done that would make this idea possible. For example, if other companies are reducing headcount with AI, investing in more AI software and AI training could yield the same results. 

Because employees often push back on these types of ideas, large company CEOs often turn to outside consultants to evaluate these options. But you don’t need a consultant to vet these ideas. 

In fact, great operators get good at running an abbreviated version of the same playbook consultants run. Even if the idea is a dud, they quickly vet the idea objectively and honestly. That way if they do end up pushing back, they’re doing it with informed judgment. 

Your playbook for evaluating your boss’s ideas

There are 3 pieces to a well-structured argument for or against an idea – and this playbook helps you make both.

Step 1: Identify the real objectives

When you hear the initial idea, don’t launch into action. Pause and ask a few questions. You need to understand what the underlying objective is behind the idea – this way, you can evaluate whether the idea will deliver on this objective, or if there’s a better way to accomplish the same goal. 

Let’s take Greg’s idea to give away 100,000 AI crash courses. There’s four things he sees as potential benefits of this strategy: increased revenue (via a sponsor or partner), PR, it shows we can scale student count, and it supports our mission. Understanding these objectives (and which are most important) helps you better vet the idea and identify if there are faster/easier/cheaper ways to deliver on the objectives.

Here’s another example: let’s say your boss tells you we should cut vendor/SaaS spend by 20%. They might be looking for $250K in annual savings, and have assumed the easiest way is to cut 20% of vendor costs. Or, they might have had a board meeting and heard from board members that most other portfolio companies are able to cut vendor costs 10-20% every two years.

You’d approach the problem differently depending on this answer. If it’s the first, you might look for other ways to cut $250K from the operating budget. If it’s the second, you know you need to focus your analysis on vendor costs.

Without knowing the real goals, you can waste a lot of time and effort. This takes some confidence, because often these ideas are thrown out as a done deal. But asking the exec what’s driving their request is critical.

Step 2: Work backwards

Assume the idea/outcome is possible – what has to be true to make it happen?

Asking this question, and working backwards from the outcome, helps you identify the constraints, parameters, and inputs to the request. And once you identify these inputs, you can make them into variables, play around with different scenarios, and evaluate the feasibility of each assumption, rather than the idea as a whole.

Let’s take the 100,000 AI crash course example – if the team currently delivers one AI crash course per month today with about 300 students per session, then we can do some quick math to identify what has to be true to deliver 100,000. One scenario might be to deliver one monthly session but put 8,000 students in each session. Another might be to increase the cohort size to 1,000 students and deliver 8 sessions per month. 

Now we know our variables are sessions per month and students per session, and we can start to dig into each variable. This includes questions like: How much does it cost us to deliver one session of 300 students a month today? How would that change if thousands of students were in the session? Or if we were running 8 sessions per month?

Identifying these assumptions helps you do two things:

1. Evaluate whether your assumptions are realistic. For example, to jump from 300 students to 8,000 students per session probably isn’t realistic within a year based on our current audience – which means we’d need a partner to help with distribution.   

2. Identify gaps or levers. In this process, we might realize that a likely scenario is 8-10 sessions per month (so 2 per week) and therefore we need an additional headcount to make this happen. Or, the product format has to change to enable delivering 2 of these sessions every week.

This is a version of napkin math – you’re breaking a large, amorphous idea down into a structure that’s easier to evaluate. Once you’ve done this, you’re ready to have a more thoughtful conversation with your boss. 

Step 3: Deliver your analysis

After you’ve done your analysis, create a 2-3 slide deck or 1-2 page memo outlining:

• The underlying goal/objective of the idea

• Your analysis around what has to be true to deliver it

• A proposed solution (one of three things)

  • Implementing the original idea

  • Implementing the original idea with adjustments (scale, timeframe, budget)

  • Implementing a different solution that delivers on the same underlying objective

Start the memo or conversation by saying “I really want to deliver on [X objective]. Here’s my analysis of what has to be true to do this, and here’s how I’d propose we move forward.”

For example, let’s say that based on our analysis on Greg’s 100,000 crash courses idea, we think that with an additional part-time resource at $5000/month, we could deliver 1 AI crash course a week with a capacity of up to 1,000 students. We would lay that out on 1-2 slides, and then say: we can accomplish your idea in two years instead of one (4 sessions/month x 1000 students x 12 months x 2 years = 100,000) and we need a budget of $60,000 per year.

Then, Greg can better evaluate and engage with the idea. This might be something we want to fund ourselves. Or this might tell us we need a sponsor that would pay $60K a year to make the program cash neutral.

Get more comfortable with personal risk

There are two skills you need for this playbook:

1. Structured thinking and napkin math – this takes time and practice. So when you get an idea from your boss or even hear an idea floated in a team meeting, practice this motion of working backwards. What are the variables to the idea, and what has to be true about those variables to make it happen? 

2. Getting more comfortable with personal risk – the hardest part of this process is making and committing to assumptions. In the example above, we don’t know if we can deliver 4 monthly sessions with 1000 students each with only a part-time resource at $5K a month. We’ve never done it before. But part of this process is putting a potential solution out there without worrying too much that you’ll be held accountable to that assumption.

If that assumption becomes part of the operating plan (i.e. we’re counting on those 4 sessions of 1000 students each a month to deliver our revenue targets) then you will be held accountable. But until then, be honest about what’s a known variable vs. what’s an assumption, and be willing to make some assumptions.

You have to do this to move the idea forward.

Our advice

Executives want to work with people that share their level of ambition. So learning how to engage with big ideas and push back without seeming unambitious is critical to your success. 

It also alleviates spinning wheels and chaos. If you ignore the idea, chances are your boss will find someone (often an external consultant) to consider it. The faster you run this playbook, the faster you stop hearing wishful thinking about this crazy idea.

You’ll usually end up with one of three outcomes:

• Green light – the idea is possible

• Yellow light – the idea is possible, but with some changes/improvements

• Red light – the idea isn’t possible or realistic

The red light is a real potential outcome, and your boss will likely still be disappointed. Don’t be shocked by this. But if they’re a strong executive, they’ll value your ability to engage with the idea. And this disappointment is a better outcome than blindly joining the skeptics or the kool-aid drinkers. 

Have a great week,

Greg & Taylor