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From the Sponsor’s Desk: Make Your Boss a Star

Has your boss ever handed you an assignment you thought was downright crazy?

Did you pull your hair out trying to figure out how to respond? Or, did you seek greener pastures to avoid the looming failure? If so, this story could provide some other options for you to consider if you encounter a similar situation in the future.

In this case, a software development manager received an undoable assignment from his boss. The manager’s response not only turned the assignment into a corporate success, but it also made him a hero and made his boss a star.

Thanks to G.A. for the facts behind this case.

Related Article: The Good Boss

The Situation

Dave, a technical manager, was responsible for a software development group that looked after the internal needs of an international technology services organization. His team had an enviable track record of successful project delivery and a very appreciative client base. Dave attributed that success to their collective obsession with client engagement, a very empowered, talented and motivated team and a passion for continuous improvement.

Dave’s boss, the Director of Solutions Delivery, was responsible for another three software development groups in addition to Dave’s team; a west coast group that focused on a diverse set of commercial clients, a centrally located organization that serviced a large number of financial services and retail clients, and an east coast team that was oriented mostly to government contracts. Those three organizations had a somewhat spotty record with their clients and a mixed record of success.

The Director had long been impressed with the achievements of Dave’s team, and he wanted to capture some of that magic in his other groups. In addition, there were five other software development groups outside of his organization that he had his eye on. These were teams that supported the business groups’ sales and service activities. The Director believed that if he could bring those five outlying teams into his organization, even on a dotted line basis, his chance of further recognition and promotion would be boosted significantly.

So the Director called Dave into his office and presented his plan. This would be Dave’s project. It would boost the company’s reputation by improving its software delivery practices, experience, and track record. It would boost Dave’s reputation as a skilled software manager, internally and externally. And, of course, that could lead to future promotions within the company and other opportunities outside.

During the meeting, Dave tried to get the Director to provide more specifics on a number of fronts:

• The burning platform? Poor performance and declining market acceptance.
• The opportunity? Increased client satisfaction leading to increased business.
• Goals? Figure it out!
• Worth? It shouldn’t cost very much.
• Requirements? Implement the practices that make Dave’s organization so successful.
• Benefits? Increased revenue and lower costs from greater productivity.
• Locations? All nine development groups.
• Target dates? You can work that out with the other managers.
• Phasing and staging needs? Give me some recommendations.
• Assumptions? Don’t assume anybody knows about this plan or buys in just yet.
• Constraints? Figure it out.
• Volumes? You figure out the number of people impacted, the number of projects involved.
• Stakeholders involved? You’ll have to bring them up to speed.

The Goal

Dave’s challenge was to identify the best practices that had made his organization so successful and implement them across all nine of the company’s software development groups. The Director provided no incremental budget and no explicit time frame although the implication was sooner rather than later.

The Project

When Dave returned to his office after the meeting with his Director, he cancelled his next meeting and started making notes about the other eight development groups and the challenges ahead. He knew all of the managers, but not well. They were geographically dispersed which made the job even harder. They had no reason to listen to him. They had their own priorities and challenges. There were over a thousand software developers and other assorted roles spread across the nine groups. He had no idea what skills and proficiencies they had. The nine groups had different markets and faced unique demands from their clients. He had no idea how many projects were in progress at any one time or the size and nature of those projects.

Dave felt overwhelmed. This was a huge job! There was no way he could do what the Director was asking along with his current job. There was no way he could do it without more money, more staff and support from the other managers, Directors and VP’s. He knew if he tackled the job under the current mandate, he’d hit a brick wall and look like an idiot in the process. And he’d make his boss look like an idiot as well. So Dave started to draft out some alternatives.

Alternative #1: This was boss’s proposal. It was undoable! He would fail. His boss would fail. It was a lose-lose proposition.


Alternative #2: Dave called this approach “Creeping Commitment” – do a little at a time, what you could manage and afford, what was supported by other managers, Directors and VP’s and communicate widely about the progress and successes. Hopefully, the approach would encourage others to get on board.


In this approach, he’d start with his three peer managers who report to his boss. His boss could establish their collective priority and make sure all were accountable for the shared results. He’d also need a project manager to run the Shared Best Practice Baseline program and four or five staff to develop the best practice repository, train the staff, and monitor practices and results.

At the same time, the Director could introduce the program to his VP and the other VP’s, Directors and managers in the other groups in the spirit of collaboration. His boss would look good as the results came in (Dave was convinced he could make some significant gains across the other three development groups) and others would be enticed to follow his lead. Win-win!

Armed with these options, Dave took the proposal to his boss. But he didn’t start out pitching his ideas. Instead, he asked his boss for advice: how could he get the other directors and managers on side, how could he get them to realign their priorities to include the Shared Best Practice Baseline program, how could he resolve conflicts over best practices, how could he reduce the risks for him and his boss if things didn’t go well. As Dave had hoped, as they talked over Dave’s questions and concerns, they started building the fundamental elements of Alternative #2: engaged stakeholders, phased development and implementation, a small team of dedicated staff, broad communication and dialogue with the other potential targets, precise goals, tracking, and reporting.

At an opportune point in the discussion, Dave asked if he could summarize their discussion so far. The Director agreed. So Dave described the discussion to that point, which was essentially Alternative #2. He drew the approach highlighted above on the Director’s whiteboard. The Director loved it! Why wouldn’t he? He thought it was his idea! He even agreed to give Dave incremental staff and budget to form the Shared Best Practice Baseline program team. Dave was a happy camper when he left that meeting. So was his boss. Win-win!

Dave arranged for the Director to update the other three managers. They collectively fleshed out the substance of Dave’s initial questions regarding the burning platform, opportunity, goals, worth and so on, until all five participants were in agreement. They also agreed on the implementation strategy going forward, focusing initially on stakeholder engagement and communication practices, then project planning and control. Dave brought on an experienced project manager to lead the best practices team, the necessary people were brought on board, and the work commenced to great expectations.

The Results

The first phase of stakeholder engagement was completed in six months in the Director’s other three development groups. Client satisfaction was up 43% across all groups. Project performance, measured on cost, time, quality and client value had improved 29%. The staff satisfaction rankings had increased 17%. Of course, these results were shared with the other VP’s, Directors and development groups. The CEO received his own personal briefing quarterly.

As they started up the second phase targeting project planning and control, the VP with four development groups under his purview negotiated with Dave’s Director to get his teams included in the program. So Dave expanded his team to cover the newly added development groups, taking them through the stakeholder engagement best practices while targeting the original three teams with the planning and control best practices.

After fourteen months, all nine development teams were in the program and a permanent core practices team was established, under Dave’s direction, of course, to facilitate compliance, performance monitoring, and new practice development. The two project teams continued to introduce new practices throughout the nine teams and leaders, and team members were often moved into the teams they were supporting to provide additional exposure and experience. Twenty-two months after that first meeting between Dave and his boss, his boss was promoted to VP of Corporate Software Solutions. Dave’s promotion to Director soon followed, reporting to the new VP, of course.

How a Great Leader Changed the Result

Dave’s response to his Director’s initial assignment was the fulcrum on which his success rested. As we’ve seen above, his choices were bang on, including the following six actions:

1. Think it through
Dave didn’t just jump at his boss’s edict. He didn’t quit in frustration. He thought the demand through, recognized what his boss was trying to do – part good but half-baked idea, part self-promotion – and came up with an approach that was manageable and would be a win-win for everyone.
2. Ask for advice
By asking for advice, Dave helped his boss think the idea through as well, building mutual understanding and shaping that original managerial whim into a reasonable, doable and beneficial change for the organization.
3. Manage up
A large part of Dave’s success was due to his team’s focus on client engagement. This initiative was no different. He knew he needed executive support to succeed. The foundation for his approach, honed with his boss’s input, was the development and cultivation of executive support at all levels of the organization.
4. Creeping commitment
The Director’s initial plan to take over all software development was a huge logistical and cultural change. It would have been met with strong resistance from all quarters. If he had pitched the idea to the CEO initially, it would have been readily rejected. By taking Dave’s “a-bit-at-a-time” approach, clearly demonstrating incremental value to the organization at each step, the potential resistance dissipated over time. Executives who would have been opposed initially instead saw the Director’s involvement as a benefit to be taken advantage of.
5. Phased delivery
Dave’s decision to phase the delivery of the best practices was critical to the project’s success. He and his new team got used to working with the other groups on a targeted change. They built rapport, cohesion, and capability a bit at a time. They experienced and celebrated success together. When they added the next best practice piece to the equation, it was just business as usual.
6. Communicate

The foundation of the project’s broad acceptance was the communication plan. This wasn’t just a monthly project status update distributed widely. It was a multi-way communication process that provided every stakeholder with the information they needed, when they needed it, in the form required. The other interested teams got timely show-and-tell sessions that related explicitly to their normal working days. Executives received the success stories, clients’ reactions, staff satisfaction numbers and results in productivity gains and quality improvements. The communication plan was actually the sales channel. And it worked marvelously.

Dave’s approach to the best practices baseline assignment ensured his success and made his boss a star. He didn’t have to invent it. He didn’t have to learn it. It was what he and his team did every day to deliver for his clients. He leveraged best practices.

So, if you find yourself in a similar situation, please put these points on your checklist of things to do in future endeavours so you too can be a Great Leader. And remember, use Project Pre-Check’s three building blocks covering the key stakeholder group, the decision management process and Decision Framework best practices right up front so you don’t overlook these key success factors.

Finally, thanks to everyone who has willingly shared your experiences for presentation in this blog. Everyone benefits. First time contributors get a copy of one of my books. Readers get insights they can apply to their own unique circumstances. So, if you have a project experience, good, bad and everything in between, send me the details and we’ll chat. I’ll write it up and, when you’re happy with the results, Project Times will post it so others can learn from your insights. Thanks

Drew Davison

Drew Davison is the owner and principal consultant at Davison Consulting and a former system development executive. He is the developer of Project Pre-Check, an innovative framework for launching projects and guiding successful project delivery, the author of Project Pre-Check - The Stakeholder Practice for Successful Business and Technology Change and Project Pre-Check FastPath - The Project Manager’s Guide to Stakeholder Management. He works with organizations that are undergoing major business and technology change to implement the empowered stakeholder groups critical to project success. Drew can be reached at [email protected].

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