Our pitches are full of must-haves. Need help to convince CEO to trust the teams!

Our 12-person startup has been using Shape Up successfully for a few months. While most of the process is working brilliantly, we do have one stumbling block.

Our CEO wants to add lots of ‘must-haves’ to the pitch so she can be sure of what we will deliver, and that it matches her ‘vision’ for the feature. We’ve found that more and more, we are describing all the smaller features in quite some detail (including polished mockups) in order to get her approval, which puts a huge pressure on the implementing team. We’re in danger of reverting to the old design/approve/implement waterfall, and it makes the ends of cycles feel like nightmare deadlines as we cram in these must-haves. Developers are starting to criticise the ‘shapers’ for adding too many ‘requirements’ in the pitch, or setting the appetite to be too restrictive. This feels all wrong!

Does the community have any tips for convincing the CEO to agree to more relaxed pitches, where only the bigger-picture elements are explicitly called-out, and to trust the implementing teams to refine the scope and find good solutions during their cycles? Thanks!


The most important thing is to look at her situation, from where she sits, and consider how Shape Up could be a win-win for both the downstream teams and her definition of progress.

The phrase “relaxed pitches” is going to sound really bad to a CEO! From her perspective, probably moving forward faster is more important. “Relaxed” is not where she wants to go! The pitches should be tight and clear about what valuable thing is going to be finished by the end of that six weeks, so whoever places the bet can say “we will have moved meaningfully forward at the end of six weeks if we do this.”

I have very little information to go on from your post, but my first instinct would be to look critically at the betting table step. I suspect that step is either not happening, or there isn’t enough negotiation taking place at that step. The CEO should have someone else who understands the costs and risks of putting too much work in a cycle at the table with her so they can push and pull on each other to figure out what goes in.

If she doesn’t see the trade-offs, and she thinks she can have it all, of course she’ll ask for it all. We’d all do that! Either someone else at the betting table can bring the trade-offs to her attention, or you’ll have to wait and let the effects accumulate until the pain of trying to do it all causes a blow-up she can see.


A few ideas that have helped me (my betting table is the company’s top two execs and myself):

  1. Inject constraints, e.g. “If we can only complete one of those must-haves in the next six weeks, which is it and why?”

  2. Focus on getting the CEO to embrace that “why?” statement to focus the pitch. So rather than a list of X features, you need to improve Y for the user/customer.

  3. Label “must-haves” 2 through n as “stretch goals” and ask the CEO to prioritize by importance. Make sure each stretch goal ties back to the “why?” to keep them honest. This may help with the negotiation part of your conversation.

  4. At the end of each cycle, remind the CEO of all the progress the team made to achieve that “why?” vision in 2. Hopefully, you delivered at least one must-have after six weeks. Charge up that “trust battery” between your delivery team and the CEO.

Like Ryan said, it’ll be critical to introduce the concept of trade-offs. Saying yes to a feature means saying no to others.

Also, it sounds like the CEO is diving into the delivery team’s flow, which may be unavoidable. Limiting scope aggressively at the betting table may help mitigate the effects of that behavior.

Dealing with execs is not easy! Be patient and try to engage your CEO in terms of incremental change vs. an all or nothing approach. Best of luck, and keep the community posted on how it goes!

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This is only realistic if you yourself play a role at the betting table.

You can’t “inject constraints” at a higher level above you. Your boss is the boss. Important to call this out and be very cautious about which pieces of advice apply to which context, depending on your role and place in the org.

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Thanks everyone for your valuable feedback. @rjs you’re definitely right that we need to advocate more strongly for the implementors during the betting table; to explain that too many stipulations in a pitch risks not delivering anything which addresses the problem, and also puts unhealthy pressure on the team. We can certainly help to guide her through the trade-offs more successfully.

However, another question now comes to mind. Perhaps we’ve been mistaken in having her too involved in the shaping process itself. Many of our pitches are self-generated, but some come directly from ideas she’s had. Either way, we currently ask her for comment before the pitch is finished, and that’s the point at which she tends to pour through the document calling out ‘must-haves’ to ensure the solution is more like the one she’s imagining. I think asking for her comment is good, but we must steer her back to the problem, rather than an obsession with describing her solution.

Her passion for describing the solution she has in mind needs to be turned into a list of benefits for the end users, and the problems they will solve. Once we’ve captured those, we can empower the implementing team to solve those same problems in their own creative way.

@rjs in general, how much comment and input do you seek from teams on a pitch before it hits the betting table? We tend to have 2-3 people involved in writing the doc, but more and more we’re getting comment from the original authors, the betting table participants and the team who is likely to be implementing the cycle. We have far too many cooks, we feel, involved in interrogating the pitch and calling out must-haves, technical issues, design ideas, etc. before we’ve even committed to working on it. I think we’re effectively doing a fair bit of the work from the start of the cycle inside the pitch doc, before we commit to it, and it becomes overly verbose and prescriptive.

Thanks again for your thoughts!

@georgecrawfor Aha I see.

Yes, in order for a pitch to be tight, the people working on it must be very small. Committees can’t make trade-offs.

Here’s how I picture it:

The time to get broad input form many people is before shaping, as an input.


I think that diagram will help us a lot, @rjs. Thanks so much for taking the time to reply. We absolutely love your work, and especially the clarity of message, so keep it up!

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ironic when the company slogan is “focus on what matters” :wink:

You could also try and get your CEO to read this book, or read it yourself and try to advocate the ideas here to her

Perhaps your CEO thinks the way to win to have more features than the competition, but many of those features are unlikely to be the reason why people sign up for the product. People don’t signup for Basecamp because of the project archive feature. They don’t signup for Gmail because of the ability to mute a sender. They discover these things later.

  1. maybe she should make an honest assessment of how the product is better and worse than other products in your space. Maybe you can play up your strengths and marketing efforts without actually covering all the features found in competing products. Often you just shouldn’t assume your customers know anything about the competitions (or if you even have competitors). You may be acutely aware of competing products, but many customers simply aren’t.

  2. It may be possible through customer discovery to uncover some underserved niche and reposition the product rather than chasing companies with larger teams who are much further down the road and much better funded.

some more great strategy books via