Quick wins, long game: Mastering transformation under pressure

There’s a seemingly contradictory aspect to transformation. While we can’t expect it to happen overnight, the moment we decide to embark on a transformation journey, the clock begins to tick, and our stakeholders are expecting to see results. In fact, many of them want to know when to expect results before we’ve even started, which is something I wrote about recently.

How do you navigate these expectations? It involves walking a fine line between what’s possible within your given timeframe and being prepared for roadblocks that may come up and prevent you from making progress. 

Let’s take a closer look at both of these topics.

Understanding your transformation timeline 

One of the hard truths about transformation is that we need to show results fast. We’re expected to show the impact of our transformation efforts within three to six months—even though true transformation takes much longer than that. Our stakeholders are ready to pull the plug and remove funding from our transformation experiment if they don’t see the immediate benefits to the business.

So how do you navigate these sometimes opposing requirements? I like to think about it as demonstrating the art of the possible. While you won’t be able to change everyone’s behaviour and attitudes, think of this initial period as an opportunity to showcase what this change could look like. And the way you’re most likely to achieve that is with a pilot team that goes through the discovery process. Let’s take a closer look at what you might expect to achieve within those critical first few months.

Knowing what’s possible to achieve initially

For your transformation to be successful, you will need to adopt a product mindset, always keeping your outcome in mind and iterating based on what you’re learning. Here are a few guiding principles to keep in mind:

  • It’s critical to identify your goals. Why are you actually doing this transformation? What's the purpose behind it? What does success look like? What do you need to shift? 

  • You also need to get leadership aligned around all of these goals. In my experience, this is never the case at the outset—especially with cross-functional leadership—so you’ll need to work together cross-functionally to define and agree on what success looks like.

  • Embark on discovery work to better understand the context you’re operating in, which involves conducting leadership interviews. Your goal from these conversations is to learn how your org is making decisions today. How are you going from a goal or idea to the everyday decisions teams are making? How is your company actually creating products today? By the way, the OMG Canvas is a free resource I’ve created that helps guide this work and keep track of what you’ve learned. 

  • When you have a current state snapshot of your product operating model, you’ll want to perform a gap analysis. What are your goals? What does the future state need to look like? 

  • And then it’s time to start creating that future that you’ve defined. But rather than expecting everyone in your organisation to get there at once, you’ll want to select a suitable pilot team. A pilot team can be much more nimble and adaptable than your entire organisation, so they’ll be much more likely to demonstrate results within those first few months. They will also learn a lot about how your plans meet with reality and what needs to be iterated or changed before rolling out new approaches to the wider team.

  • When it comes to selecting your pilot team and the project they’re working on, here are a few points to keep in mind: You want people who have the right mindset and experience working this way—or at least the desire to do so. And you’ll need to walk a fine line between picking a product that’s too small and inconsequential or too big/mission-critical that it puts your entire business at risk. 

It’s only then—once you've got your pilot team in place and they have some guidance on what you would like to do differently—that you'll start to see some results.

Everything I’ve just outlined here is what needs to happen in the first three to six months. I’ll be honest—this is a really short timeframe for this work, especially if you have a diverse and large organisation. But committing to this initial push is often required if you want to be able to bring transformation to the broader org.

Be aware of these potential roadblocks that might slow your progress

You might start with the best of intentions, but roadblocks could still derail your transformation efforts. Here are a few of the usual suspects prevalent in many orgs, to help you prepare and be ready to spot and mitigate them early:

  • You encounter the inability or unwillingness to change: This can manifest in many different ways throughout your organisation, whether it’s the inability to change measures of success (“Everyone has to enter their OKRs into the same system and we can’t change that”), the inability to change the way projects get funded, or the inability to truly shift to an outcome mindset. Another way of phrasing this is that people are shifting toward the desired new approaches, but the system says no.

  • You discover you don’t have the right people in the right roles: There are different ways you might encounter this roadblock as well, such as only getting pilot team members who can work on the transformation project part-time or as a side project, managers from other departments who won’t give their people permission to work cross-functionally, or a lack of people within your organisation with the right capabilities and no budget to hire external people. 

  • Your organisation doesn’t support learning: It takes time and space for people to learn new skills, and they may need support in the form of training, courses, coaching, etc. But if your organisation doesn’t have budget or allow people time to focus on learning, it’s going to be difficult to succeed with your pilot project since it’s essentially all about learning. Another way you might encounter this roadblock is that teams are expected to execute flawlessly. But that’s not how learning works. If we truly expect people to learn, we need to give them space to make mistakes and then make adjustments based on what they learn. They need to be able to adapt when their plans hit reality.

What comes next?

My goal in outlining these roadblocks is not to discourage you, but simply to make you aware of some of the challenges you’re likely to face. With this knowledge, you can begin to anticipate how you might prepare for and mitigate these obstacles. 

This is also why I emphasised understanding the context you’re operating in during the initial phases. Going through an exercise like taking stock of your current state with the OMG Canvas will give you a better idea of what you’re up against and where you’re most likely to encounter resistance.

And remember that you don’t have to go through this on your own. If you’re looking for someone who’s been there and who can help guide you and your organisation through transformation, get in touch to learn how Northshore can support your efforts.

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