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Where is Your Roadmap Taking You?

Updated: Aug 4, 2021

You may have seen the cartoon about the lumberjack who emphatically declared he was far too busy with far too many trees to cut down to take time out to see the pesky salesperson— who was offering chainsaws.


Now is a good time to set down that well-worn axe for a minute and think about that never-ending project list that you keep adding to weekly, and why you need to think differently about your "digital roadmap".


No roadmap will work if you aren’t clear on the destination. Even worse, what if you follow it to what turns out to be the wrong destination?

A community bank CEO we’ll call Megan recently showed me a full-page grid from an expensive consultant’s report she had just commissioned. Her bank’s name headed the first column, with the remaining columns headed by about eight competitors of various sizes. Each row listed a digital capability like ‘video chat’, ‘mobile account opening’, 'mobile loan application’, and so on. The column for her bank had a couple of check marks in it, but it was noticeably empty relative to the other columns. The largest bank on the list had a check mark in nearly every row.


“Everybody’s to-do lists just got a lot longer after I got this.” she sighed, “We’re even further behind than I thought. We’re using this to create our digital roadmap, what do you think?”


I scanned the grid and asked “So, you decided that the purpose of your roadmap is to get you to a place where you eventually have the same capabilities of your largest competitor, who has a budget at least a hundred times larger than yours?


I had gotten to know Megan fairly well. I spent a half day with her board and executive management team a few months ago, and one of things we talked about was choosing strategically where to play offense versus defense. Everyone liked that way of looking at it, and we had a robust discussion about how to best prioritize what are always limited resources. Her new head of digital strategy quipped that it sounded like “Moneyball”. I suggested some tangible next steps at the end of the meeting, and they said they’d get back to me right away. They were excited to get started.



"We're not ready yet"


After a few unreturned follow-up emails, Megan finally told me they decided they "weren’t ready” to play offense yet. They had too much catch-up work to do updating and replacing legacy systems. She also told me that they hired an expensive consultant to help them create a digital roadmap. When she got it she asked if I would look at it and give her my thoughts. I said It looked more like a laundry list than a roadmap.


Megan frowned and looked off to the side for a minute. “This is going to be very expensive. The board is asking about ROI, and the consultant is being pretty cagey about that. How do we know what we should do first?”


“Not only do they have a bigger budget, they have a really broad and diverse customer base.” I told her, “Not all of these things are important to everyone, and I thought we agreed that you won’t win by trying to be a smaller version of them. When we met last time you had some really good ideas for doubling down on a segment of your customers where you were already winning against your biggest competitors. If it were up to me, I’d start with something that can extend that competitive advantage. I’d play Moneyball, as (her new head of digital strategy) Marcus put it. Do you want to win the contest for the most check marks on an arbitrary list of features, or do you want to win the game?”


"Do you want to win the contest for the most check marks on an arbitrary list of features, or do you want to win the game?”

She smiled at that. The last time we were together the mention of "Moneyball" led us to discover our shared love for soccer, and we learned that our favorite teams were huge rivals. She teased me that my team didn’t show up very high on the list of team payrolls, and nowhere near the top of most money spent on new players in the past ten years. She said my team didn’t seem very ambitious. I pointed out that during that same timeframe her team had made the playoffs 5 times and won two major trophies. My team made the playoffs every single year, played in four finals, won two championships, and added three other trophies. My team played the game to win, not show up on pundits’ lists, I told her.


She got the reference immediately. “We want to win the game. She declared, as she looked at the grid again. Then she just couldn’t help trolling me again. Just like (her favorite team) will when we play again next month…”


No roadmap will work if you aren’t clear on the destination. Even worse, what if you follow it to what turns out to be the wrong destination?


Not every box needs a check mark.


Not every box needs a check mark, and you can't win every arms race. You need to decide which are the ones that will help you stay in the game, and which ones will help you win the game.


Your organization is never going to be more “ready” to make the changes you need to make. You need to make them anyway.


That day when all of this craziness will die down isn’t coming. You need to act now.


The answer isn’t finding the right vendor.


Your IT department can’t do it for you.


Your vendors can’t do it for you.


That hot new fintech startup you just discovered can’t do it for you.


That all sounds good, but we’re just not ready yet.


This is usually a way to articulate a fear that’s understandable and hard to describe. A fear of the unknown. And a comfort in the known, even if it’s less than ideal. Bankers are trained to be risk managers, but we often take too much of a binary view of risk. We tend to view things as either risky or not risky, but of course there are a million shades of gray in between. What’s the risk of not acting soon enough?


The most important part of every journey is taking that first step.


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