Managed Self-Conflict: Training Project Managers to Anticipate and Navigate Challenges

Hi! I’m Natalie Tarasova, Head of the Project Office at Imaga. Today, I want to discuss one of the most crucial skills in custom development: the ability to forecast. In other words, forecasting means meeting expectations — especially your own. This skill will be valuable for all project managers and their leaders.

In custom development, we refine our forecasting skills every day. The longer a specialist works in the agency business, the better they become at it. Questions like, “How can we get developers to provide more accurate estimates?” almost always come from those outside of custom development, often from product teams.

But team leads are better suited to discuss developers. I’d like to focus on the managers.

How We Forecast at Imaga

At Imaga, all project managers are involved in management accounting. Each PM (Project Manager) is expected to forecast project volumes and the accuracy of these forecasts is crucial — it’s easier to handle a predictable decline in volume than an unexpected drop.

Unexpected growth has its pitfalls too. It can cause production bottlenecks and lead to significant, though less obvious, issues such as management planning errors.

For instance, a PM wasn’t sure if the client would assign more work to the project and told the management not to expect additional funds. During this time, the leadership was deciding whether to host an important meetup that could attract new clients. Since no extra funds were expected, they decided not to hold the meetup. Eventually, the client extended the contract and brought in more money, but the opportunity to host the meetup and attract new clients was missed. The missed opportunity did manage to leave a bitter taste.

And that’s a mild example. Company leaders handle numerous issues, most of which involve financial decisions. They must know about incoming or outgoing funds in advance to make informed decisions. Should we hire a new specialist with a high salary? Or should we keep the current one and give them a raise? Maybe buy that second office fridge everyone’s been waiting for? All of this requires planning. As a manager, you’re either aiding this process or hindering it.

How to Achieve Effective Planning

Clear planning is straightforward: set up protocols, organize the process, and track it regularly. Everyone does it one way or another. But how do you ensure effective planning from each participant?

Almost everyone uses the same method, but either they don’t want to admit it or adapt it and give it a different name. There’s probably a fancy term for it in psychology, like manipulation (which I don’t like), but I call this method “managed self-conflict.”

The main goal of self-conflict is to make the person you’re questioning doubt all possible answers, but still navigate the boundaries and come out with an accurate prediction.

At Imaga, we plan three months ahead: the current month plus the next two. During this period, the PM needs to understand what to expect from the project clearly: the client’s backlog, any team changes, and when we’ll finalize results and get sign-offs.

For an inexperienced manager, all these questions can be terrifying. How can I pinpoint the exact time when the client will approve everything? What if they don’t want to? What if we don’t make it on time? Out of fear, an inexperienced manager might become overly pessimistic or excessively trusting, making promises they can’t keep. Both scenarios are non-starters.

Here’s where the leader’s assistance is crucial. Their job isn’t just to provide answers to questions, but to teach a manager how to make forecasts and stand by them, even if it means fighting tooth and nail for them.

Training can be gentle or tough — it depends on the leader. I’m all for effectiveness, so it’s essential to understand the motives and character of the manager from the get-go. Here are a few examples:

It’s crucial to recognize these behavioral patterns early, not confuse them, and understand what the manager prioritizes — accuracy in forecasts or personal motives. The leader’s goal should be to ensure the former.

Next comes the core. We need to ensure that the manager:

• Understood that every forecast can be questioned;
• Started doubting their own decisions;
• Adjusts forecasts together with the leader, and eventually, on their own;
• Gradually calibrated and improved their forecasting skills;
• Ultimately learned to prepare answers even before questions are brought up;
• Learned to forecast better than the leader.

Example 1: “Let’s add one more month on top”

Background: Design concept work. Closing with an invoice of 20 thousand USD is scheduled in two weeks.

At this point, the manager has shaken the confidence of the PM (and also questioned the client’s sanity). Now the PM is ready to push back the project deadline. But the project is in its final stages, and waiting another month for its completion is out of the question. Here, the manager begins to steer in another direction:

In this completely fictional but realistic-sounding dialogue, we were able to accomplish the following:

• Addressed project risks.
• Emphasized the PM’s accountability for outcomes and timelines.
• Prevented the project from sinking into a quagmire where nobody knows when it will end.
• Encouraged the PM to think broadly about factors that could impact the project.
• Highlighted the importance of risks by illustrating the difference between adequate and inadequate handling.

Example 2: “How do you predict that? No way to predict it. But you can anticipate the risk.”

Background: The developer has been working on the project for six months. He consistently completes tasks and meets targets.

We can’t predict with 100% certainty what tomorrow will bring, even with the most reliable developer. Let alone looking months ahead. But we don’t disregard the “reliability factor”; instead, we incorporate it as one of the criteria when planning our work.

A 10–15% margin won’t derail the overall planning. It’s important for the PM to recognize that this is just a form of pessimism, not an infallible plan. This should be clear to the manager and anyone with whom the PM shares their plan.

At the same time, we shouldn’t overplay risk management and suggest the safest minimum amount of work in case of a volcanic eruption. Plus, it’s always worth considering the project’s potential for growth, which pushes planning towards the positive side.

Example 3: “So, we’re doubling down on risk.”

Background: We’re preparing a schedule for the client, who already has precise project delivery deadlines. The project manager drafted a schedule that perfectly aligns with the client’s expectations. Suspicious? That’s an understatement.

You didn’t break the project manager’s work and didn’t make them fear project challenges. On the contrary, you agree that the schedule is decent, but there are risky spots that can be fixed without sacrificing deadlines. You also increased the project manager’s confidence in thorough planning, while anticipating unforeseen events.

Self-Conflict Checklist

Certainly, at first, you’ll need to engage in these philosophical dialogues frequently. Over time, however, these questions will become a mental checklist for the project manager when planning a budget. These self-reflective questions create an internal dialogue, a form of self-conflict. They may vary but share a common theme of doubt. Some of the questions we need to kickstart are:

• Will the task be completed within the timeframe I set (or was given)?
• Will the task be approved on schedule according to the contract?
• Will our contractors let us down?
• Do our budget expectations align with the client’s?
• Are there any contentious issues in the task that might arise?
• Will each participant deliver as expected based on the percentage of time allocated to them?
• Is everyone involved aware of and agrees with the arrangements made?

And the opposite doubt:

• Is this really all we can do?
• Will it really take that long?
• Can’t we find a way to be more efficient?
• Aren’t we expected to come up with new ideas and suggestions?
• Are we sure the client won’t like new ideas and suggestions?
• Do I know the team well enough to align my expectations with my plans?
• Have I made this plan rationally and not just because I felt pressured?

These questions are incredibly annoying, aren’t they? But you must learn to answer them first and then confidently defend your decisions to your higher-ups.

In my examples, I used a mixed planning approach, but it’s better to do it step-by-step:

1. In the first meeting, discuss all the potential risks and create a worst-case scenario.
2. In the second meeting, say a week later, shift from the worst-case scenario to exploring opportunities instead of focusing on risks.
3. As you progress, continue to refine your approach and move toward success.

It might seem like you’re putting the project manager through an emotional roller coaster and pushing them into constant doubt. However, this internal conflict can help the manager become a true professional, handling challenges better than their boss.

Most importantly, don’t overdo it. Find the right approach for each person. Good luck!