Long-term projects need significant investments upfront but promise to provide high value in the future. You can lose your investment if you don’t manage them well.

Example, OpenAI started years before they became famous for ChatGPT. They spent a lot of time and money working towards their long-term goal. Their leaders had to overcome many challenges to reach the milestone.

While today I don’t talk about how to manage a large company, this article focuses on the challenges you should watch out for when starting a long-term project with a large team. This is an important skill for all leaders.

I have completed several multi-year projects for our Meta’s internal cloud. I have encountered many challenges and learned some valuable lessons. Today, I am sharing these lessons so that you do not have to repeat my mistakes.

Let’s dive in.

1. Prioritizing Hard Problems

Long-term projects solve complex problems. They have many subproblems that have to come together for overall success. Those subproblems may seem urgent and important, but in reality you have limited time and resources. So, you cannot make meaningful progress in all of them.

You need to ruthlessly deprioritize hard problems to make room for the most important ones. This will be a constant process every planning cycle.

For me, long term projects run for multiple years and the planning cycle is every 6 months. So, adjust these suggestions for your durations.

Recommendation

• Trim down your core goals / MVP to the essential must-haves. Ask yourself these questions:

  • Will your core goal be affected if you don’t address this sub-problem?

  • What is the cost to the business or the opportunity cost if you postpone a sub-goal?

  • Will it impact team productivity? If yes, by how much?

• Balance depth and breadth

  • At the beginning of the project, choose problems that only < 50% of your team can handle. Use the rest of the time to delve into depth and address other surprises.

  • Don’t postpone complex and hard problems until the very end. They may require expensive re-engineering later in the project life cycle.

• Review your plans with leadership and the business. If you don’t prioritize solving real business problems, your team will have to shuffle projects later.

2. Dealing with Hidden Work

No amount of planning can catch all hidden work. While experience from past projects and diligent reviews help identify many, they are not a substitute for the production signals. When a real customer uses the system you build, it will reveal workflow and reliability gaps.

I have found that people often underestimate the amount of hidden work that can shuffle their priorities. I am a pessimist, so I always expect something to come along the way. While I don’t add too much buffer for them, I readjust our goals when they come up.

Recommendation

• Err on the side of going to production “soon”

• Find a use case that leverages your project while it is still in progress

• Work towards enabling at least one critical use case in production

That will generate more work, so be ready!

3. Managing Attrition

This is an unavoidable part of any project, and you cannot be prepared for all departures. When critical engineers leave, it will cause major churn and delay your commitments.

Recommendation

• Have multiple people for important areas to ensure redundancy.

• Do adjust your goals when they leave! Don’t make the remaining team overwork to accomplish the same goals, or else they will leave too.

• Document decisions and constraints so that people taking over don’t need to redo them.

4. Staging the Value

Everyone wants ROI sooner. This is true for long-term projects as well. Waiting a few years for that impact to land can be undesirable for the business. That way, if the project stalls, it has still had a positive outcome thus far. So, build milestones that provide you with real impact. Also, hitting these intermediate milestones gives the team something to celebrate, which boosts morale.

Recommendation

• You can enable it for X% of customers or production requests.

• Consider targeting customers who bring in the most $$$ or have high costs.

• Prioritize real, pressing problems first and enable your solution for them.

It is a constant struggle for me to balance near-term milestones with long-term focus. Near-term work can take up more time, which could derail long-term work. At the same time, you have to deliver these near-term milestones to prove the value.

5. Adapting to Changing Constraints

2022 showed us that market conditions change, which affects funding and priorities. Long-term projects are under extra scrutiny.

Recommendation

While you cannot control and prevent all conditions, you should:

• Document assumptions and expected improvements to key metrics. That makes adjustments easier.

• Plan for “unexpected” changes upfront so that when they arise, you have a runbook to follow.

• Pivot instead of chasing the previously defined goals.

6. Maintaining Confidence and Perception

Project perception is important. It not only helps the team stay motivated but also gives the management reasons not to axe the project. If your partners and stakeholders don’t see the value, they will lose interest.

In my experience, most people don’t voice their concerns until it is too late. The perception problems snowball in people’s minds over time.

Recommendation

• Have frequent project updates and celebrate your milestones.

• Conduct tech talks with project Q&A.

• If you messed up something, share what you learned with the rest of the company.

7. Having a concrete timeline

People get obsessed with finding an exact completion time. You cannot anticipate all hidden issues thereby an exact completion time.

Recommendation

• Articulate that the project is going to take at least X years. Never overcommit.

  • Overcommitting and underperforming is a classic recipe for losing confidence in the project.

• Highlight the value generated by each milestone. Timelines for the milestones in the near term should be firm.

• Highlight milestones with uncertain timelines and provide reasons why.

Long-term projects require effective management and leadership for success. Have you encountered any other problems that you have had to deal with?

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