It’s impossible to get our exec team to focus on one segment. How do I balance prioritizing my roadmap while building for different segments?

I deal with this a fair emount in my current role - Delivery at ezCater to some degree touches all possible users of our multi-sided marketplace (customers, supply & fulfillment partners, internal staff), and each of those major user buckets contains multiple segments.

Here are some things I've found useful in dealing with all these different user segments at once:

• First, acknowledging to yourself, your team and your stakeholders that there are A LOT of potential problems to solve, and complex effects of focusing on one segment over another - but trying to serve all at once runs the risk of slowing down progress. Simply put, acknowledging the challenge itself helps me because I've often found that folks underestimate the challenge of having to build for many users at once.
• Deepen your knowledge on the relative value (current and opportunistic) of each segment, and possible network effects that occur by affecting change on one or several of them. For instance: improving the experience for a non-revenue-generating user (eg. internal staff) may not drive money directly, but may provide better experiences for revenue-generating users or save costs to fund other initiatives elsewhere.
• Look for opportunities to solve many problems for different segments or user types at once. This may be via network effects (eg. improving the experience for power users allows you to charge them more, enabling you to lower prices for new customers or invest elsewhere), or by building with multiple users' in mind (eg. building a tool for new customers that, with a small addition to scope, also helps power users).
• All the while, look for opportunities for quick wins or learnings to keep pace up and iteratively create value.
• All the while, working with leadership to understand the current or potential value of each segment to help steer you in the right direction.

It is natural for leaders to be ambitious and get enticed by potential growth segments. To avoid confusion and inefficiencies with the organization’s limited resources, leaders need to identify a primary customer segment that the product truly solves for, while exploring other segments for long-term opportunities. 

Start by using data to identify a primary segment that aligns with company strategy and vision, and get executive buy-in to focus primarily on that segment. Clarify that you plan on exploring ancillary segments with limited scope in the roadmap and the consequences of spreading the organization thin including a failure to achieve company goals. Finally, work with executives to define goals for each segment to determine what to include on the roadmap and ensure the product and organization is best set up for success.

This can happen because your product growth potential is sufficiently broad across multiple customer segments or you may be operating a complex product surface that serves different segments (eg: multi-sided marketplace). 

Turn this impossible situation around, instead of asking your execs to pick one segment (which seems limiting), focus on prioritization. 

• Align with your exec on the primary customer segment or priority order of customer segments. This will unblock roadmap prioritization for your teams.

• Reiterate how choices, trade-offs, and investments re-affirm the aligned customer segment priority with your execs when presenting the roadmap.

• Periodically review customer segment priority with market data to ensure your product strategy evolves as your business grows.

Don't force them to say no, get them to say "Hell Yes!"

If the leadership team is not willing to commit to one segment, and you believe that's needed to succeed, then don't make them choose. Get them excited about a specific segment and how it is the fastest path to achieving their goals.

Once you have them excited, it will be easier to align them on funding the work that is needed to unlock the opportunities in that segment and pull resources from other projects.

That is a hard situation to be in. Here are some options to try

• Communicate your roadmap to the executive team organized by segments, showcase what you can prioritize for a segment and what you cant with the latter focusing on multiple priorities across various segments being the primary reason why you can't create focus for your team

• Create a focus segment for a given planning cycle, eg: Q1 on Segment 1, Q2, Segment 2, etc

• Identifying common use cases across segments

• Identifying platform features that enable multiple use cases across segments

• Prioritizing features across all segments with the help of a framework (ICE: Impact, Confidence, Effort)

I think executives in all shape and form need guidance from domain experts. They are looking for product leaders to have confidence in their conviction and share the same confidence with executives.

I usually form my opinions based on data and experience with the help of my team and then present to executives, reiterate multiple times with the help of visuals and then share broadly with teams after alignment. Sometimes, I'd use competitive (e.g. a market is already saturated in a particular segment) or complimentary examples (e.g. a company in an adjacent category focussed on a certain market and gained traction and similar parameters apply to us) to signal a GTM move that can benefit or not benefit us.

Ultimately, you have to show the executives path forward with a plan A and a plan B (backup) when deciding on a market.

This is often the case for companies in a hyper-growth state, especially as they look to find a clear fit in the market. Where I've found success with leadership is by helping them understand the trade-offs in our teams focus.

For example, when planning out our team's work, we lean heavily on research and a few key metrics to prioritize. When faced with requests from leadership that may not align, we try to create an apples to apples comparison (though not always perfect) to help bring clarity to the trade-off.

Two things are critical here:

• Being clear about the capacity of the team, and the realistic implications of having to trade-off (vs attempting to do both simultaneously)

• Leaning on data wherever possible. Data is not biased, and likely will help leadership understand your perspectives if the segment that you're looking to focus on differs from the ask.

Executives that can't provide focus for your team can be a common situation when there's early stage market uncertainty and pressure to do customer discovery and find PMF. Top company leadership feels an intense time pressure (I've heard it described as a holding both a compass and a stopwatch), and so is reluctant to reduce potential segments that could become winners. More than anything here, they're hoping for some signal/data/customer success that could then increase the certainty of focusing on a single target market segment and product direction.

A lack of leadership direction can also occur in more stable product/business situations when leaders don't understand the tradeoffs that are implied in what they're asking for. E.g. a leader who's never been a PM, designer, or engineer may just keep asking for more features which could help with sales, expecting the team to push back or explain when they can't do everything asked of them.

The solution is in closing the gap in understanding. When leaders ask for too much, the team can't do a good job in serving or even learning about all the different potential customers. Execution suffers and delivery dates slip. Product quality suffers which leads to tech debt and more time wasted fighting bugs and regressions vs. building new things.

Here's a template for broaching these topics when requests push you into the danger zone:

1. Boss, you asked for X+Y+Z.

2. Here are the best plans we can come up with for X+Y+Z if timing is fixed and resources are fixed.

3. All of these plans are pretty shitty and will likely result in product failure due to reasons foo and bar.

4. Here's a plan we think is better if we relax the timing constraint or the staffing constraint.

E.g. after being asked to pursue many customer segments simultaneously:

1. Illustrate what it looks like in terms of a project roadmap and timeline to try to serve all those customer segments.

2. Be super honest about the risk of failure in all segments.

3. Offer alternatives that relax the timing constraint:

   1. MVP learning in all segments simultaneously, but little to no product development until we've chosen the 1-2 most promising segments.

   2. Sequencing segments over time: 1-2 segments first so that you can credibly learn about their needs, try to serve them, and evaluate whether you could reach PMF.

   3. Serving one segment super well, but doing learning exercises in adjacent segments.

4. Offer alternatives that relax the staffing contraint:

   1. Outline what you think is a reasonable number of segments to make a credible effort with >50% chance of success with current staffing.

   2. Outline how much increased staffing would allow you to make a credible effort with >50% chance of success on all the additional customer segments.