Taking Control: How One Exec Team Reclaimed Their Tech Strategy

[00:00:00] Welcome to the Convergence Podcast. I'm your host, Ashok Sivanand. On this show, we'll deconstruct the best practices, principles, and the underlying philosophies behind the most engaged product teams who ship the most successful products. This is what teams are made of.

[00:00:25] Hey folks, welcome back to another episode of the Convergence.fm Podcast. Today, I want to walk you through a story, one that started out with a frustrated CEO, a legacy system that they were using, and a team that was stuck. More importantly, it's a story about momentum, clarity, and how good facilitation can be super powerful in unlocking strategic decision-making and building momentum.

[00:00:53] So let me give you a little context on what was going on. This company, a customer of ours, had a technology system that was very expensive. It was built and configured a long time ago by the prior leadership system, and no one really loved using it. As the new leadership team got settled in, they started to notice the friction, and the system wasn't just frustrating, it was slowing the team down.

[00:01:17] It kept the folks stuck in a cycle of reactive work, and it wasn't allowing them to focus on the strategic initiatives compared to the firefighting. Think things like their white glove services, they couldn't scale to their customers because of the way the data flowed or didn't flow. And then, boom, the vendor hit them with a double-digit price increase. That's when the CEO reached out and said,

[00:01:43] Hey, I'm in need of someone who understands technology to help think through a few things that we're working on here at the organization. I've talked to a few people, but I don't feel like anyone I know and trust isn't trying to just sell me something versus help us solve our problem.

[00:02:00] He continued to talk about the product they were using and how it integrated across various departments, and how they wanted to find new options before that contract ended with a really tight deadline. And he said, I'm not sure we're even asking the right questions or seeing all the options in front of us. Now, that kind of message, it's certainly a flag.

[00:02:24] Not just that the system's broken, but that the process for evaluating what's next and getting moving is also at risk. Clearly, the stakes were high. If they pick the wrong solution, they don't just lose the money. They risk staff efficiency and morale and future revenue and realizing the vision that this new leadership team is trying to redirect them towards. So here's what our team did.

[00:02:50] We got them unstuck by running a two-day workshop and helped them move from being stuck to feeling like they had strategic alignment. And I'm going to talk about what we did. So of the two days, we started with day one around focusing on clarity, priorities and alignment. We brought nine of their stakeholders together from various departments and we split them into groups of three. And we'll get into why later.

[00:03:16] And we started the day with a playful icebreaker to set the tone that focused the team, but also energize everyone in the room. Then we asked the CEO to reiterate the company vision, not just the surface level mission, but a pointed narrative about how technology was going to become an enabler going forward and no longer an obstacle. From there, we got to work.

[00:03:39] Each person rolled up their sleeves and we had them work on sticky notes, working individually at first to brainstorm their goals for the department and how they were going to align to the vision and surface that into a reality together. We then had them filter them as their departmental groups. And then most importantly, we had them prioritize them. We use a stack rank initially, which is a top down list where there's no equal priorities.

[00:04:07] And then now that we have a sense of the vision of the organization, how the different departments are going to help get there. We wanted to talk about what's getting in the way, the risks. And we did the same thing. We did a solo brainstorm, group deduplication using stack ranking. And then we prioritize in this case using a two by two matrix. And we mapped out these assumptions by impact and certainty. And we surface the most dangerous assumptions, the ones with the highest impact and the lowest certainty that allowed us to focus.

[00:04:38] And so each team ended up designing experiments to validate or de-risk those assumptions as part of the broader goal. So now we've got goals and risks both prioritized. So we zoomed in even further. This time on user stories. Each of the folks mapped out the user stories that they wanted the system to be able to surface. As an X user, I want to do Y so I can achieve Z. Now it's hard work imagining what matters most when you can't have everything.

[00:05:07] But when we tied it back to the risks, the goals and the visions, it gave the folks a way to gut check their prioritization. So with that, we were able to wrap the day up. And at Integral, we like to end most of our days with a plus delta L. What do we love about the day? The plus. The delta, what do we want to change about tomorrow? And the L, what's the most meaningful thing we learned? So the team left feeling like they had a sense of closure and very energized. And what did we have?

[00:05:37] Within one day of work, we had prioritized goals that surfaced the vision of the organization. We had prioritized risks and experiments. And then we had prioritized user stories for the new system. This gave us enough context and priority that we could draft an RFP as well as a scoring rubric for a new system. A pro tip, we use ChatGPT to generate the early versions of both of these.

[00:06:03] And that allowed us to spend a lot more time refining instead of reinventing. That moves us to day two, where we focused on data, drafts and decisions. Our goal for day two was to first think about integrations, which came up as a risk across all the departments. So we had folks work again individually around what data they need, where they need it from, and what the value and what difference they could make if they had this data.

[00:06:29] Again, we worked solo, then group, then across the organization. And some data pipelines were critical and daily. Others were quarterly board meetings fluff. So we knew what would drive the most ROI from automation. We mapped them, prioritized them, and then we added them to the RFP draft that we got from ChatGPT. And then we had the team look at this draft. The silent self-read, we called it.

[00:06:57] And we handed each stakeholder the draft RFP and rubric. They read, scored, reacted. Again, first individually, then together as groups. And they had debates around clarity, weightage in the rubric, and drove home what really mattered. And what we landed with is a draft RFP that was highly validated at this point internally to the organization, that reflected the company's goals, not just one of their vendors' architecture.

[00:07:25] We also used a scoring rubric as a benchmark by evaluating their current system against the rubric. And then a team helped build the artifacts together. So it meant that they had a sense of ownership and pride for these two documents now. And for me, most importantly, they were moving forward and they were no longer unstuck. What they thought would take three to four weeks, we managed to get done in a matter of two days or just 16 work hours.

[00:07:53] If you're running your own workshop or thinking about something similar to unlock a tough decision, especially if it has expensive tech like this one, here's a few things that made a big difference for us. The first one was solo work before group work. I believe that individual thinking before group consensus allows for individual ideas to the surface, reduces self-censorship and unlocks the best ideas from the team. For the workshop nerds, there's some things you can go deeper on,

[00:08:23] like using the same Sharpies, the same color Sharpies, having everyone write in caps. So I'd remove this bias on whose idea it is and prioritize the best ideas. Starting big and then going narrow. Diverge to gather all the ideas and then converge to prioritize. We use different prioritization tools, whether it's dot voting, stack ranking, two by twos. They're useful in different contexts. Groups of three. I think three is an important number. There's enough folks on the group that bring a lot of value,

[00:08:51] but not a ton of coordination overhead of having four or more people figure things out together. And then the last one is action items and next steps. We made sure that we prioritize action items at the end of the session too, so that folks knew the next morning what they were going to go work on and no longer be stuck. I think this shows that the right facilitation paired with a good, trustable technology perspective can turn what felt like chaos into actionable clarity.

[00:09:17] And it can unlock weeks of effort just by having a couple of days of collective unblocked work. Another thing that we did here was that we made sure that this was a no technology day. We had ample breaks, we had ample snacks and make sure folks were fueled and energized, but also focused. And so this required a little bit of prep and making sure that everyone knew a couple of days prior so that they could turn on their out of office responses and other things like delegation. So they could focus for both of these days.

[00:09:45] So if you're stuck or gearing up for a big decision, especially an expensive one, and you want some help or a soundboard on your workshop, hit us up, DMs on X, LinkedIn or Instagram, or drop us a note at convergence.fm on our contact us page. We would love to nerd out with you and help you with that or facilitate it for you. And we'll be back next week with another episode about fostering engaged teams who ship delightful products.

[00:10:13] Until then, I hope you have a wonderful week. Thank you so much for listening. Thank you for joining me on the Convergence podcast today. Subscribe to the Convergence podcast on Apple Podcasts, Spotify, YouTube, or wherever you get your content. If you're listening and found this helpful, please give us a five-star review.

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