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Leadership, Project Management

How to Become a More Challenging Project Leader

If you want to be a strong project manager and leader, you need to know how to challenge and support your team members in equal measure. This means that you are able to set clear performance targets that stretch the individual while at the same time providing them with the support they need to reach their targets. While it might sound easy in theory, it’s far more difficult in practice.

During my years of project management coaching, I’ve come across a large number of PMs who feel competent in the area of being supportive and nurturing but find it far harder to be challenging and to set the standard. When these leaders try to challenge a team member—for example holding them accountable to goals—they often lose their confidence in the process, which leads to questioning themselves or stopping in their tracks because they fear that their words will be too harsh and hurtful.

Inside these leaders know what they want to say, but they have difficulties formulating the words because they worry they’ll either upset the other person or the words will be taken in the wrong way. As many project managers put a high value on personal relationships and harmony, they end up holding themselves back when they have to deliver a message that could be interpreted as critical. For some leaders, when they do say something direct or challenging, they become overly apologetic afterward and backtrack. The result: delivering mixed messages, which is not a strong position to lead from.

Why your team needs to be challenged

If you recognize yourself in the above description, you first need to consider that you may well be doing people a disfavor by not holding them to account. If you let people coast or get away with poor performance, you are contributing to their decay.

For the most part, your team members will find it motivating to learn and grow and to know that you, their manager, will expect the best from them. In addition, these individuals will feel more confident and in demand if their skills, abilities, and performance are on par with—or better than—that of their peers.

If you challenge people to stretch and move outside of their comfort zone in the right way, you’re helping them in their career. What you also need to remember is that with your continued support your team members will be well placed to meet the expectations you’re setting. I’m in no way implying that you should begin to be a hard-nosed boss and that you should stop being supportive.

Set expectations, agree on the outcome

A really big point, which I hope will help you to appropriately challenge your team, is that you need to mutually agree on performance expectations up front when you assign a task. It’s almost impossible to hold someone to account if you haven’t been explicit about the details of what was expected and what a good outcome looks like. It’s imperative, however, that the performance expectations are mutually agreed upon, and that it isn’t just the project manager who sets the standard and decides what the task looks like and when it needs to get done by. If it’s a one-sided expectation exchange the team member will not buy into it and will not perform well.

But how do you agree to these performance expectations in a way that enables you to better challenge the team member? Let’s look at an example.

Let’s say that you want a team member to create a presentation, which she will give at the project kick-off meeting. As you delegate this task, ensure that you and the team member have mutually agreed on answers to the following questions:

What is the scope of the task? The first question you need to answer is what exactly the team member will deliver at the end of the assignment and what “good” looks like. To help you clarify what is expected from the presentation, make use of the MoSCoW method (Must have, Should have, Could have, Will not have). In this case, it could mean that the presentation must be in PowerPoint, it must have 8-10 slides and it must be able to be presented within a timeframe of 20-30 minutes. Each slide should contain a visual element and should have a clear message or take away related to the topic. The presentation could be printed for each participant, but will not be provided in electronic format. The presentation will have screenshots but will not encompass a live demo. Before handing in the presentation it must be spell checked and should be peer reviewed.

How much effort is involved? Estimating how much effort is involved in creating the presentation will be much easier now that you have agreed to the scope of it by using the MoSCoW technique. The next step is to help the team member think through what the best-case and worst-case estimates are until you reach a realistic assessment. Don’t estimate the work for that person, but ask clarifying questions that help you both understand the reasoning behind the estimate.

When can the work be delivered? It’s important that you don’t set the deadlines and give team members full ownership of finish dates. What you can do instead is help people think through all the work that needs to be completed, what could slow things down, and from that information what date are reasonable to commit to. When team members set the deadlines themselves they’re more inclined to take ownership of reaching it and living up to it.

What could go wrong? Before you finalize finish dates, ask the team member to consider everything that could get in the way or prevent him from delivering the task at the agreed upon date. In other words, help team members think through all the risks involved and how to overcome or mitigate them. Not everyone is wired to think about their tasks and workload in a logical way, so use your skills to help them organize their work.

What support do you need? Now that you’ve agreed on what needs to get done, when it will be completed by, and what the potential roadblocks are, it’s appropriate to ask the team member what support they need from you. Maybe she would like to practice a dry run of her presentation with you or have the green light to ask someone a teammate to peer review it. If you want to stretch, challenge and hold your team member to account, you need to ensure you have done everything you can to set them up for success, so ask them what support they reasonably need from you or anyone else.

How, and how often will we check in? The last question is about how you’ll check in with individuals to assess progress. Regular one-on-ones are needed for a team member to ask for guidance, feedback, and support. What you don’t want is to come across as a controlling micromanager, so agree up front on how and how often you’ll meet and don’t overdo it.

For example, consider the following: Will you check in with each other every other day via telephone, once a week face-to-face or will the team member keep you updated with a weekly progress report. Agree to a form that will work for both of you and stick to it unless you agree otherwise.

Based on this kind of expectation exchange, it should be clear that you have set the team member up for success and given them the best possible conditions for delivering a great presentation. If an individual ends up not delivering what you both agreed to, you now have a contract to reference and a framework that will help you hold team members accountable.

The big difference with being an effective challenging leader is that you’re not holding them to your standers, but to the standards that you both agreed on. In truth, most people are happy to be held accountable for delivering results provided they have a say in their process and received support getting there.

Leading teams effectively is one of the many exciting project management challenges you face! To learn how to lead great teams and master the trickery of your job, download our eBook, How to Solve the Top 9 Project Management Challenges.