Rasheen texted Mike in great excitement and suggested they meet for lunch that day. After the waiter had taken their orders Mike got right to the point.

Mike: Alright, Rasheen. Spill the beans. What’s got you so hyped up?

Rasheen: My brother-in-law went to this workshop on AI with all his managers. He was freaked out at before he went because his company wants to move fast to adopt AI tools but no-one seems to really know how to go about it, but he came back totally pumped and optimistic. And guess what? The workshop wasn’t even about AI.

Mike: What? How does that work?

Rasheen: Well, they did talk about AI, but the workshop was about something else. It was about a system to get everyone on the same page about what they wanted to achieve and what might get in their way.

Mike: OK, that sounds interesting. But how did that make a difference for him to go from freaked out to pumped?

Rasheen: Think about it. What’s your biggest challenge right now?

Mike: Well, I have a lot on my plate and now I’m supposed to champion more change that I don’t know much about. I can’t explain it to my team or the project team. I don’t want to look stupid or create more stress for them. And I don’t see a clear path through it.

Rasheen: Exactly! And what else?

Mike: What do you mean?

Rasheen: Why don’t you just tell your boss how you feel?

Mike: Yeah, right. And risk looking like a whiner or a resistor. I want to impress her and get a promotion.

Rasheen: So, the problem is all about communication. There are lots of gaps and misunderstandings. Nobody sees the whole picture, all the risks and potential.

Mike: Yep. That’s pretty much it.

Rasheen: Well, in the workshop they learned a system to close those gaps and create a shared vision. They used a simple tool that helped them all get on the same page.

Mike: Really? How did that work?

Rasheen: They all agreed on what they could potentially achieve for the organization, their customers, and themselves. And they also identified their top challenges and risks.

Mike: Seriously, they all agreed?

Rasheen: Pretty much, and now they all have some homework to do. They have to read some articles, watch some videos, and do an exercise to prepare for their next workshop. They’re going to figure out an initial roadmap for their AI journey.

Mike: Wow, that sounds impressive. But what excited your brother-in-law the most?

Rasheen: He said that everyone understands and believes in what they are trying to achieve and they had the best session ever with their director who usually is kind of hard to discuss ideas with.

Mike: So, don’t leave me hanging. How did the workshop help them do this?

Rasheen: They used a tool that made it easy for them to discuss their aspirations and concerns about using AI with each other and their teams. Even though they were clueless at first and had lots of questions. And then he and the other managers used the tool to put together the big picture with the ideas and hurdles for each team and showed it to the director. It was all laid out on one page so the director could easily see what the teams were thinking and what some of the barriers might be. Almost immediately the director noticed a couple of things that were at odds with the vision and they discussed it and cleared it up right away. Then the director went through the hurdles and they clarified the ones he didn't understand. Best of all my brother-in-law said, there was no frustrating all-managers meeting where some people get lost, and a few hog the floor, the director gets irritated and most people feel like their concerns were not heard. He left the meeting feeling like everyone was on the same page and could see the potential value and his director understood their concerns.

Mike: So how can we get our hands on this tool? Maybe it will help me get the direction and information I need from our executive.

Rasheen: I'm texting my brother-in-law right now to ask him.

Rasheen and Mike ended their chat with a big "aha!" moment: mobilizing change is like navigating a sailing ship through unfamiliar waters to a new destination. They've got to see the execs' big picture, discover the details relevant for their crew on deck, and raise risks and ideas back up to leadership. It's like translating a foreign language without a dictionary—tricky but oh-so-rewarding when it clicks.

Middle managers need to be expert translators, turning exec-speak into action steps their teams can accomplish. But let's face it, sometimes trying to grasp those strategy communications is more like spotting shapes in the clouds in the sky than seeing directions on a map. Often, middle managers need to play detective, piecing together clues to make sense of the grand plan. It's a game of back-and-forth, building the map and asking execs to fill in the blanks. The secret sauce is to create a structure for a strategy map that minimizes the amount of translation managers need to do without drawing executive into the weeds.

Sure, there'll be times when the team's got a question about the strategy and the manager's drawing a blank. It's all part of the dynamic communication to uncover the path forward make sure everyone's moving to the same beat.

With transformational change it's seldom possible for executive to know exactly how their vision will play out on the ground, especially when it comes to big shifts like going digital or integrating AI. Execs are too far removed from daily operations. Middle managers and their crews are on the front lines, spotting the everyday hurdles and hiccups that can trip up these big plans. But it can be a real puzzle for managers to quickly inform execs about risks and ideas without getting so bogged down in details that the big picture gets lost in a fog.

So, sparking real transformation is less about perfecting directives handed down from high and more about embracing a collective conversation. It's a dynamic process where the vision and the map emerge in greater clarity as questions spark dialogue, and where everyone's two cents can lead to a dollar's worth of innovation. It's about crafting a culture where uncertainty isn't a roadblock, but a stepping stone, and the solution is sculpted through everyone's hands-on participation. In this space, learning to be comfortable with the unknown is key, because as the plan unfolds and evolves with each contribution, clarity emerges from the collective effort.

Let's take a deeper dive into the critical process of executing strategic transformation by envisioning it as seafaring voyage.

At the helm is the executive, the captain who charts a bold course across the high seas of competition and the rapidly evolving digital ecosystem. They steer the organization towards grand objectives, with a keen eye on delivering value to their customers. The project executive, much like the first mate, breaks down these broad strokes into actionable directives, rallying the crew for the journey ahead.

Middle managers, serve as the navigators and boatswains of this vessel. They are vital for charting the journey and keeping the voyage on track.

As navigators, middle managers take the captain’s vision and the first mate's directives, translating them into a detailed map. They plot the course, marking the route with waypoints that signal key milestone in four areas:

 1. Hitting organization goals,

 2. Delivering customer value,

 3. Building capabilities, and

 4. Developing talent.

Every sailor knows you need to set waypoints so that you can determine if and how much you are being blown off course in time to make the right small adjustments to reach your destination. Your organization goals and your customer value aspirations describe the fundamental purpose of the transformation - the end of the journey. Capability milestones and talent development describe the means to reach your destination. Every digital transformation requires new organization capabilities for decision making and planning and new capabilities for supporting the digital technology.

Every digital transformation also requires new skills, expertise and mindsets throughout the organization for mobilizing change. Capabilities and talents are the critical means, in addition to technology and training, for achieving your ends, your transformation purpose. Capability and talent waypoints are the early indicators of being on or off course and middle managers are the closest to understanding the status of these indicators.

As boatswains, middle managers then turn this map with its waypoints into activity plans, assigning specific tasks to their teams. Middle managers are the critical link between strategy and execution. They ensure that every member of the crew knows their role and how they fits into the larger picture. Middle managers adjust the sails – the team's focus and efforts – to catch the winds of opportunity and avoid dangerous currents and to navigate through the storms of uncertainty.

Success in digital transformation does not follow a fixed linear course. It is a dynamic, responsive voyage that requires agility and adaptability. It requires readiness to tack and jibe, to handle known and unknown obstacles like submerged rocks and uncharted shoals. And, as the journey unfolds, the charted course must be adapted and plans revised, informed by the influence of the dynamic environment.

In this story of strategic transformation, the executive, project executive, and middle managers all play interconnected roles, each vital to steering the organization not just towards reaching its next destination, but towards thriving in the vast and unpredictable ocean of rapidly accelerating digital evolution.

At the helm of any change initiative lies a critical question: where is the organization headed? An unclear or misinterpreted understanding of the intended strategic direction is at the heart of millions of dollars of cost overruns, countless hours of wasted time and energy and a significant source of stress for everyone. As navigators charting the course, middle managers need to accurately understand the direction in which the organization is headed.

The first part of the strategic direction is the destination - the 'why' behind the new direction. Many times there are unarticulated assumptions within the communication of strategy. This easily happens when executive spend hours evolving and discussing the strategy and then attempt to synthesize all that into a precise presentation or document. Most people are blind to their own assumptions in their communication and it is up to middle managers to ask questions and ensure their interpretation is what executive intended. And of course middle managers are often blind to their own assumptions as well.

One way to speed up this process of ferreting out Assumptions Is to very explicitly Articulate The outcomes Of this strategic direction. That is. What exactly are executive expecting Will be achieved for the organization and how will they know the extent of the benefit of this achievement for the organization. In other words how will the achievement be measured?

In Mike's case he knows that his company is embarking on a digital transformation by introducing a new system to automate workflow and enhance digital services for customers. Take a moment and ask yourself what is "why" behind this digital transformation? What are the big picture objectives?

Well, you might say the objectives are to automate workflow and enhance digital services for customers. This sounds clear at first but then ask yourself what are the outcomes for the organization? For example,

• How will the organization benefit from automating workflow?
• Will it save money by laying off people?
• Will it improve customer experience by delivering services more rapidly and attract more or bigger customers?
• Will it free up managers' time to think and plan strategically rather than struggle endlessly to keep up with all the tasks coming across their desk and thus achieve better ROI from their  other strategic initiatives?
• Will it empower employees to do more value add work such as delivering more personalized service to customers and increasing customer loyalty and customer lifetime value?

Mike cannot answer this question right now, not to himself and not to his team. He has a choice to either make an assumption or ask his boss. If he makes the wrong assumption he may lead his team in completely the wrong direction or at a minimum create a lot of unnecessary confusion and stress. If he asks his boss there is a good chance he may find that his boss actually isn't clear either. And what if his boss has made her own assumptions which do not match the assumptions of the executive team and communicates her assumptions to Mike as fact? And even more confusing, what if people on the executive team have different assumptions? 

Alright, let’s navigate Mike’s quest to unearth the core reason—the “why”—behind the company’s move towards automation.

First let's talk about what Mike should not do. Mike needs to sidestep lobbing a vague, broad-spectrum question like, “Why automate?” at his boss. That’s a surefire way to either get a foggy answer wrapped in assumptions or that raised-eyebrow look that silently questions his grasp on how automation creates efficiency. However, just being efficient doesn’t cut to the heart of the benefit for the company. Mike’s still in the dark about the real prize of this efficiency.

To keep the conversation with his ever-busy boss focused and short, Mike can pinpoint one specific outcome and probe its accuracy. He could brace for impact and pick the outcome that his team is most likely to assume — that automation might just be the corporate speak for cost-cutting with layoffs as the punchline.

But then, a lightbulb moment! Mike considers that there’s likely a set of outcomes that this change could bring about. So, he decides to lay out potential outcomes on the table, ask for confirmation and if there’s anything he's missed.

Here is the email Mike sends to his boss.

Dear Rachelle,

Thank you for the opportunity to be up on stage with you during the launch of our digital transformation project. To prepare for that event and to ensure I can provide the best leadership to my department I would like to gain further clarity on the outcomes that the executives are expecting. It's important for me to ensure everyone has a clear understanding of the desired results.

From our previous discussions, I understand that one of the objectives of the project is to automate workflows. To prepare for the inevitable questions from my staff I have outlined several potential outcomes that I believe could be associated with automating workflows:

1. Increased Cost Savings: Streamlining processes through automation to increase efficiency and reduce operational costs by laying off or reallocating staff.
2. Enhanced Customer Experience: By delivering services more swiftly, we have the opportunity to improve the overall customer experience, fostering greater satisfaction and loyalty and increasing customer lifetime value.
3. Enhanced Strategic Focus: Automating routine tasks could free up managerial time, allowing us to focus more on strategic planning and critical decision-making.
4. Employee Empowerment: Automation can empower our employees to engage in more value-added activities, such as providing personalized services to customers, or providing insightful information for management decisions.

Your insights on which of these outcomes are expected by the executive, as well as any additional expectations that the executives might have will help me communicate the right messages to my department. This will ensure that our efforts are aligned with the organization's vision and goals.

Do you have time to connect this week to discuss this further or would you prefer to communicate via email?

I look forward to your guidance.

Best regards,

Mike

Notice that Mike frames the outcomes in ways that could be measured; number of staff executing the process, human resource costs, service delivery time, management time allocation, level of personalized service, quantity and quality of information provided to management.

Also notice that Mike specifically asks for confirmation of executive expectations, not his boss's expectations. This encourages his boss to be accountable for ensuring she has clearly received and understood executive expectations. 

Although more senior than him, Mike's boss is also being squeezed and experiencing many of the same challenges as him. Ideally she would have asked executive to clarify the visions as part of ramping up to lead the project. Even more ideally executive would have walked through the process of defining measurable outcomes expected for this strategic initiative. But even when the start of change is less than ideal, (which seems to happen a lot) middle managers can still initiate a process to set and communicate a clear direction and purpose. 

As Mike suspected, his boss had not received clear communication on the expected outcomes either. She replied to him that she didn't expect any staff layoffs but that she had forwarded his email to the executive team for confirmation and would get back to him. 

This interaction between Mike and his boss brings up critical power pointer around understanding the perspective of senior management. Mike knows his boss is also very busy. She has a heavy operational responsibility and is in the midst of a large, high profile service expansion. She has scarce time and energy to lead this digital transformation. So she will appreciate anything he can do that does not increase her workload.

Mike's email was quick and easy to read and understand. He opened with the context of his question, explained the reason behind his question and provided potential answers for executive to confirm. Because the email was precise and clear she could easily forward it to her boss adding a couple of sentences of her own and maybe adding an additional outcome she was assuming.   

While Mike's in a holding pattern for his boss's feedback, he starts thinking about understanding the destination of this transformation for customers. He's clued in that this is all about sprucing up the digital journey for clients, yet he's scratching his head over the specifics. "Will the customers tango with the new automated workflows?" he muses. So he shoots off an email to the project manager, asking for the specific on how the customers will benefit.

Mike groans when he receives the response from the project manager - two long documents. One document is the project charter - 67 pages long. The other document is the business requirements for the customer portal - over 100 pages. There is no way Mike has time to read these tomes so he does a quick search for 'customer benefit'.

He strikes it rich in the business requirements doc. It's not just a list of benefits, which, by the way, were as clear as mud in the charter. It breaks down the customer landscape and their current challenges interacting with his company. For each customer segment it explains how the new system and processes will simplify their experience, save them time and get money back in their hands quicker.

Using this information it takes Mike no time at all to fill out the customer value section of the strategy value map template that Rasheen's brother-in-law had given her.

Next Mike moves on to the employee section of the strategy value map. This section describes the value of the transformation for the employees who will need to change the way they work. Although the project charter lists the impacted departments, Mike decides to break down who is impacted by primary job role. He does this for two reasons.

He's got an inkling that this change isn't one-size-fits-all; it's going to ripple through his department in a kaleidoscope of ways, touching each role differently. Plus he suspects not everyone in the flagged departments will feel the tremors of change.

A couple of days later Mike receives a reply from his boss answering most of his questions about the expected change outcomes and scheduling a meeting to discuss it further. This is good news for Mike!

He rolls up his sleeves and fleshes out the first slice of the strategy value map with the insights he's gathered. This map's going to be his North Star in the upcoming discussion with his boss. To make sure his compass is pointing true north, Mike huddles up with Rasheen for a quick once-over of the map's maiden voyage before setting sail into his boss's office.

Rasheen is excited. She gets the point of the transformation and understands the benefit for all the groups involved. And it only took her a couple of minutes to read.

Now Mike is ready to meet with his boss and make sure he is clear on the strategic vision for the customer, the strategic direction for the organization and the strategic value for employees.

The meeting between Mike and his boss goes very well. His boss likes the diagram because it is informative and quick to read. She doesn’t have time to search through documents and has not been able to acquire a communications person yet for the project. She is not sure if the list of impacted job roles is fully complete and suggests that Mike organize a meeting with the managers of each of the impacted departments to explain the project purpose and verify the list before the project launch video conference.

Score for Mike!

He is affirmed in his leadership role

He feels more confident he can at least answer the questions from his team and his peers about the purpose and direction of the transformation.

He already has the strategy value map that he can use to guide the conversation. No other preparation is needed.  

Middle managers can begin to escape the squeeze by freeing their feet from a traditional linear approach and learning how to

Navigate Change:

• Middle managers are the indispensable navigators and boatswains of change, not just executing orders but actively shaping the journey.
• They translate the captains' (executives') strategic vision into day-to-day actions and decisions for the crew (employees).

Cultivate a Dynamic Dialogue:

• Real transformation blooms from lively collective conversations, not just top-down directives.
• Questions and open dialogue clarify the vision, allowing each team member's input to fuel innovation.

Embrace the Unknown:

• A culture that sees uncertainty as a stepping stone, not a roadblock, is key to adaptive and successful change.
• Solutions are crafted through everyone's participation, evolving with the journey and contributing to the clarity of the collective goal.

Chart the course with measurable waypoints

• Build alignment and across the four aspects of transformation:
• Achieving organizational goals, 
• Enhancing customer value,
• Building internal capabilities,
• Fostering talent development.
• Enable early and frequent small adjustments and avoid being blown way off course

Use the Strategy Value Map as their compass:

• A visual codex that encapsulates the transformation objectives for the organization and its customers, and the value of the voyage for all on board.
• A bridge connecting the strategizers with the doers on the deck, ensuring the message rings clear and consistent to everyone.

By taking a different approach and embracing this change action system, middle managers can reduce their translation and communication effort, propelling the ship forward with a shared language and a unified direction that keeps everyone on board working in synchronicity. 

In the next chapter we will follow Mike as he uses another tool - the Change Adoption Canvas - to onboard his managers and understand their questions and concerns.

Thank you so much for reading this rough draft.

Thank you for taking a couple of minutes to respond to the questions below.

I greatly appreciate your honest answers so that we can spark hope and confidence in middle managers to escape the squeeze and confidently mobilize change.

Louise