Skip to content or call us at ‪(240) 630-4674‬
2040's Ideas and Innovations Newsletter Image Header
What Would You Do?

What Would You Do?

Issue 128, September 28, 2023

We’ve all been in business situations that are uncomfortable, confrontational, and dysfunctional. Even after spending decades building a career, we can get a curveball that puts us in an untenable position.

In our newsletters we seek to surface new ideas and realities of the workplace, always recognizing that the human factor is always of paramount importance and influence. It is our intention to help you and your organization manage change, successfully transform, and adapt to an ever-evolving marketplace.

We have covered topics and explorations focused on leadership, communication, workforce alignment, and more. In that regard, we hope we have given you the perspective, tools, and approaches that assist you in looking at situations, problems — and yes even innovations — in a new, informed light.

We remain advocates of modern, enlightened leadership, which has become table stakes in managing a generation of younger workers who have changed the rules of engagement. Although a top-down, command-and-control management style has never been appropriate in any business organization as a pathway to a highly effective workplace culture, it is especially irrelevant today. And that’s just one paradigm shift that is redefining the workforce.

So, today we’re going to focus on the curveballs. Those unexpected left turns that we experience from time to time that often come as an unpleasant surprise. The lens is an interactive “what would you do” exercise. Put yourself into the story we present and decide how you would deal with the circumstances we describe. And if you enjoy this type of strategic exercise, you’ll love our book, The Truth About Transformation, which offers plenty more!

Is this Ship Going to Sink?

This is a true story.

Olivia, the editor/publisher of a small digital B2B brand for C-level beauty business executives has been successfully running her niche media company for 15 years. With five employees and a roster of freelance content creators, the brand makes a modest profit. She has built a loyal community of readers and collaborative partners.

The brand is a division of a larger media organization owned by private investors that plays in the fashion/style/beauty arena. She and her four employees have worked together for so long that they understand each other in shorthand and even anticipate what someone else is going to say. Their mutual respect and shared purpose keep the business on track, even during challenging times or when they outwardly and noisily disagree. They agree to disagree as long as it furthers the business. Each plays a role that supports the brand and keeps everyone else grounded and focused. It’s a self-organizing work model that Olivia supports resulting in constructive and proven outcomes.

Change of Leadership

Then one day, seemingly without need or cause, the investors appoint a new CEO for the parent organization that houses the media brand. Frances, the new executive, comes from a non-media background but has been recognized as a sharp leader who has a proven track record of ramping up profits for legacy brands. She hits the ground running and is shaking up the organization with new systems and procedures. She has turned her attention to the niche media brand but has spent little time or effort with the brand’s team to understand its audience, operations, or revenue model.

Her major innovation for the organization, and now for the media brand, is to outsource all marketing to the firm she has worked with for over 20 years. Her past experience has validated that there are efficiencies resulting from outsourcing the marketing function.

She is dependent on Rob, the founder of the marketing agency, and is convinced he is a genius in marketing strategy and operations. However, neither Rob nor Frances has experience in running a content and media brand that is recognized as a thought leader in its niche.

Rob is a shrewd operator and knows how to play up to the CEO, stroking her ego, appealing to her vanity, and managing her expectations. He’s good at it and has established a two-decade rapport with Frances.

Power Positioning

Here’s what happens next. Olivia is told by Frances that her life is going to get a lot easier; the agency will handle all marketing, promotion, email operations, social campaigns, and pricing for partnership programs. Olivia is told she is liberated to work on leveling up the content, spend time developing new business and re-envisioning what the brand could become. No distractions with running so many of the daily operations. And she lost three of her employees in the transition, so she is now going it alone with the one other remaining staffer.

Olivia’s first encounter with Rob does not go well. She is told that all content will be organized into an automated system and stringent deadlines must be maintained. Her writers will receive automated prompts to invoice the agency which will process all payments. The agency’s team will manage all design, marketing copywriting, and workflow. It’s important to interject at this point that the agency has never worked on a daily digital media brand.

Innovation Theater

Olivia is skeptical but has no choice but to go along with the flow. And here’s how the first six months unfolded.

Rob convinces Frances that the brand needs to be rebranded and refreshed. To do that, he and Frances hired a third-party qualitative researcher to review the brand, its content and value proposition. Olivia is asked to provide contact information for stakeholders to the researcher for her investigation.

The branding exercise drones on for months. The agency, although diligent and methodical, is painfully slow. The momentum for running the brand is compromised as Olivia and her skeleton team operate without agency … and enthusiasm. The brand has gone from nimble to hobbled.

In the meantime, the agency proceeds to automate the content distribution with new database management software and eliminates the analytics dashboard Olivia has relied on to keep on trend with how the content is resonating. Rob increasingly presents innovations that Olivia and her team experimented with years ago and dismissed because they were ineffective. And when she asks Rob why he is demanding her writers’ contact information she is told, “You obviously have trust issues. You don’t get to ask me why. When I ask for something, you deliver it.”


The war of wills escalates. As does a string of avoidable mistakes. Content is posted on the website before it’s marketed. The images associated with the daily reports devolve into the level of a high school newspaper design aesthetic. The marketing copy supporting partner webcasts is sophomoric and event messaging is buried at the bottom of the daily emails. Rob refuses to photoshop supplied images claiming they are unacceptable. He refuses to help Olivia set up a new analytics dashboard because he doesn’t have time. He tells her not to change a word on any of the sales proposals. The automated prompt for the writers doesn’t work. Olivia now has to describe in detail what images she wants, a task her former design director knew intuitively. Basically, Rob leaves an indelible impression on Olivia that she works for him.

Rob is a quintessential command and control manager. He is arrogant, abusive in tone and borderline misogynist. He is obsequious with Frances and imperious with Olivia. He demonstrates confusing passive/aggressive behavior. One moment only too eager to help, the next judgmental and alienating. He is an anachronism.

Olivia sees the brand she has built become compromised and at risk of becoming irrelevant. She is excluded from creative decisions and isolated from business decisions with clients she has nurtured for years.

What Would You Do?

So, what would you do? Put yourself in Olivia’s place.

  • How would you navigate the devolving situation?
  • Is it time to flee or rise to the occasion and find a path to constructively move forward?
  • As change is always underway, is the situation just an example of organic transition? How should it be managed? Or is it a situation of a disaster unfolding without guardrails?
  • If you were Olivia’s coach, how would you advise her?

Now, if you were Frances:

  • What might you have considered before applying efficiency models that are familiar to you but may not be relevant to the niche media brand?
  • What might you have considered before forcing a marketing agency on the media brand?
  • How would you manage Olivia during the initial stage to make the transition work smoothly?
  • If you were Frances’s coach, how would you advise her?

Transformation Is a Moving Target

Change is never easy. Our humanity leads us to hold on to what is comfortable, what is known, and expected results. When change is thrust upon us, particularly, when we are not the initiator of the change, we become frustrated and filled with anxiety, and our world suddenly becomes less clear. As change agents, we stand for new ideas and innovations, but context always remains paramount to success. What works in one situation often doesn’t work in another. Cookie-cutter approaches, particularly those pulled from past experiences, are often disconnected from the function and outcomes of an organization that is not exactly like the one where the previous approach was taken.

Humans, for all of their similarities, are still egocentric. They are often wedded to their way of thinking and doing things, even if it may compromise the success of a group. Power and control as a shield for insecurity often derail empathy and understanding. So, on the one hand, when we are stuck in our ways, we may be insensitive emotionally and intellectually to a different approach. If we are out of touch with how others are motivated and can succeed, we may come across as a steamroller.

“What would you do” is a metaphor for walking in someone else’s shoes, as a way to reveal how we can think differently. In any organization, walking in your colleagues’ or workers’ shoes is essential to effective communication and leadership. Using a case study that objectifies behavior and attitude is a good way to look at problem-solving that isn’t personal.

So, we recommend you take any dysfunctional situation you may experience, turn it into a third-party narrative and spend some productive time determining what you would do. It may sound like a gimmick, but it’s a great way to take a step back and see the situation from several perspectives. And ultimately, it leads to a solution. We promise!

Get “The Truth about Transformation”

The Truth about Transformation Book Cover ImageThe 2040 construct to change and transformation. What’s the biggest reason organizations fail?  They don’t honor, respect, and acknowledge the human factor.  We have compiled a playbook for organizations of all sizes to consider all the elements that comprise change and we have included some provocative case studies that illustrate how transformation can quickly derail.

Order your copy today and let us know what you think!

Back To Top