Project Management, Leadership

What Keeps Even the Best Project Leaders Awake at Night?


On any given day projects are complicated. When complexities give rise to uncertainty and issues, it can cost even the best project leaders many rough sleepless nights. Regardless of project skill or experience, any Project Manager can — and will — find themselves faced with multiple factors that can decrease the chances of success and increase the risks of failure.

Here we shared what several project managers said keeps them awake at night.

Rachel Jacobs is Brand Manager for and works along side her in-house team of three and remote team of five. She says her most sleepless nights are due to:

  1. Managing an in-house team
  2. Time zone differences for remote work
  3. Answering for every outcome, including bad news

Rachel explains, “I deliberately hired people with talent over experience, and in some cases, I see their talent more than they do. As a manager, I take it as my responsibility to develop and grow each member of the team individually and push them to challenge themselves by stepping outside their comfort zone and trying new things. This consumes a considerable amount of time, and more than that it consumes a lot of my emotional time as I am invested in their success and have great expectations for them that sometimes can fall short.”  

Due to time zone differences, she works from 5am to 11pm, six days a week, sometimes seven days, which doesn’t leave much time for rest. Another thing that impacts her sleep is having to “answer for every outcome, good, or bad, on behalf of the team, justify every expense, as well as manage this process. So, as you can see there are a lot of moving pieces and a lot of things that keep me awake at night.”

Mark Tuchscherer, President of Geeks Chicago says the two biggest factors that create sleepless nights for his team are:

  1. Timeline delays
  2. Budget overruns

Mark says “We run into many situations that result in delayed sprints and tasks which are not completed on time. This can delay the overall project, and clients are never happy about that. Also, when things run over, the budget can be impacted, which is always a major issue. Telling a client that something has run over budget is not a conversation any project lead wants to have.”

Jon M Quigley, Founder of Value Transformation LLC says these areas can disrupt any project expert’s sleep:

  1. Issues with scope clarity and fluctuations
  2. Resource availability
  3. Schedule pressures
  4. Communication blockages


Jon says where project scope is concerned “the lack of clarity or the fluctuations in the project scope. It is not unheard of for the customers to either not have a solid understanding of the scope of the project or an inability to technically articulate the entire boundaries of the scope. In these instances, the contract for the project may be secured based upon this loose scope and there will be many subsequent changes. These changes can slow down the project as the project is inundated with change requests that require approval and coordination. In the worst incarnation, these changes are not understood, not coordinated and not taken into account for the cost and schedule impacts, but just acted upon. This situation is much slower and costly due to rework. Even if there is a good understanding of the scope, it is possible to fall into this trap through informal (often verbal or email) change requests without a systems view. The project manager is often not privy to this backroom communication and therefore will not know there is even the possibility of a problem until the parts are put together and the change is discovered, often at the customer site.”

How can a project leader get a better night’s sleep?

When laying awake at night pondering problems and solutions, try to remember you aren’t alone; open and frequent dialogue is key. Discuss issues with the team, stakeholders, and leadership and strive to leverage their expertise as partners. Make use of collaboration tools to help solve any communication disconnect as a result of distance. Maintain focus on stakeholder needs and project goals, and recognize it may be necessary to slow things down temporarily. Be transparent and solidify expectations before charging through to the finish line only to find out you’ve missed the mark.