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Manage when leadership is in trouble

Many of us have been at work managing a project or advancing a new initiative, and leaders overseeing the work can get lost in unnecessary detail. How do you manage so that the project doesn’t lose momentum? Using a real-life scenario of how a director at a tech company can build a disposition model to simplify sales and show it to his leader and the salespeople who use it, the authors suggest three strategies to keep leaders out of the project weeds: 1) with you 2) Sales Global, 3) Create Self-Service Content.

In the midst of high growth, salespeople at a global technology company are confused about which customers and opportunities to focus on. Mark is the new head of the IPO team and he is leading a project to build a propensity model to address this issue. The model collects numerous data points across different systems to provide targeted leads to salespeople. Leaders are excited about the model and the problems it will solve, but they often end up getting bogged down in the details during the presentation. Mark started to get frustrated. How can he get his leaders out of the woods so that he can move forward with this important work? Individuals at all levels of an organization experience situations where leaders lose the big picture. We’ve been in this situation throughout our careers, starting with small projects with bosses and later presenting transformation plans to the board. While the specific issues in these cases are different, the underlying challenges remain the same. Based on more than 30 years of experience influencing leadership decisions, we suggest three steps individuals can take to reset their conversations with leaders. We’ll demonstrate these steps with a real-world example of how Mark, a new director of a $10 billion global technology company, has successfully advanced his work in a series of detailed questions.


talking to salesperson , Mark kept hearing the same thing: “I don’t know where to focus.” Most salespeople have dozens of accounts, and the company sells a range of products with new releases every month, which means some people don’t like it. Feel overwhelmed with the products they have to sell. As a result, the company’s sales pipeline did not evolve as expected, and leadership became nervous. Mark has been with the company for over a year and has just been promoted. He has built-in support and a desire to take on a big problem, and he’s excited to think that’s it. Working with a data scientist, Mark overcame significant technical challenges and quickly built a dashboard that clearly showed salespeople where opportunities were in their region. When dashboards are released in small numbers, salespeople are enthusiastic, and leaders want to hear more. The meeting quickly turned into a drag, though, as many leaders focused on adoption data (one of the types of data used in the model) and system issues since the company had many reporting tools. Their concerns are justified, but Mark doesn’t see the need to stop working. Disappointed with how things had unfolded, he decided to change tactics.

Moving forward At the meeting with the leader After a wave of internal meetings, Mark took a three-pronged approach. We have found that these strategies work in many situations when leaders are in trouble.

1. Work with your “users”. Individuals must see themselves as product managers and their work as “products” and move with users. Leaders who get bogged down in details are rarely the end users of their jobs. Individuals should continue to work with users, accept needs, make updates, and demonstrate value. The lack of full leadership support should not be a hindrance. Conversely, leaders are more supportive when actual users have strong enthusiasm. In Mark’s case, although he was presenting to leadership, the users he worked for were salespeople. Mark decided to continue working with sales to understand what they liked about the dashboard and what should be improved, just like he was a product manager. He continues to develop the tool based on their feedback. In addition, he has salespeople present when he trains them on enablement or meets with leadership. This positive feedback shows leaders the value of the project and leads them to spend more time thinking about how to scale their work and less time questioning the nuances of the data.

2. Sell big pictures.

While giving presentations, project leaders sometimes resort to talking about the work in a project management setting where they will take on the vision support, then move on to the executive side, sharing the GANNT diagram and discussing roles and responsibilities. This is a mistake. Instead, individuals should paint a picture of how the work will solve pressing problems by discussing the vision and use cases, and linking the work to leadership priorities. After some initial discussions with the leaders, Mark created a separate presentation for them. The presentation focused on how the tool can make life easier for salespeople, which will improve the sales pipeline, increase employee satisfaction and reduce turnover, a leadership priority. Mark is still ready to talk about release schedules and workflow owners, but he’s never led with those views. The meetings started to go smoother, and executives breathed a sigh of relief with a move that could help stem the tide of employee departures.

3. Create self-service content. Project managers should create self-service content that addresses technical issues. If two or more leaders ask the same question, it’s a good sign that it will come up again. Individuals should prepare simple FAQs, descriptions or video tutorials to address these issues and should post them on accessible forums. This will reduce the time they spend answering the same questions. Propensity models include product adoption data because monitoring customer adoption of new products is a company priority. Mark realizes that leaders are stuck in the way data is calculated. Working with data scientists and product teams, he created a page on definitions and another page on FAQs about data, which he then posted on the company’s intranet site. For a more technical audience, he sent out self-service content ahead of the presentation. With fewer questions from leadership about adoption, Mark was better able to focus meetings on key projects.

Gradually return Of course, Regardless, challenges will arise. Leadership may want to make changes to the work, or they may want to link it to other ongoing related projects. This is just part of an important initiative. In Mark’s case, the leaders initially wanted Mark to align with other internal data initiatives. Those moves, though, have been slow, fully consistent with how they would jeopardize his project’s ability to deliver value quickly. As Mark successfully used all three strategies, the leadership jumped in, and the leaders started telling other project managers to follow his work—not the other way around. The benefits of overcoming these challenges are enormous. When this kind of work is implemented, the company is better off, and the team that gets the job done will reap the benefits. What’s more, individuals in the program will improve their skills, overcome internal barriers and gain the support of leaders in the process. In this case study, change takes time. But a few weeks after deploying these strategies, Mark realized that the tone of these leadership meetings had gradually shifted from skepticism to excitement. The potential of his project has yet to be realized, but he knows he has developed a new set of skills, and the leadership of the company is on his side.



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