What makes projects so difficult to manage?
As a project manager, you need to assess the culture, your role, your team, how problems escalate, what your responsibilities are and how to tackle edge cases (delays, problematic team members, running out of budget, handling scope creep, disagreeing with a client, etc.)
Organizations that use proven project management practices waste 28 times less money than those that do not have practices in place.
Source: Visual Planning
And within the right environment, everyone follows the company mission statement and the core principles of the organization. This will turn your decision-making process into a quantifiable, well-oiled machine, which should facilitate the team and get the work done.
Project management is, in theory, the activity of ensuring a project’s success within an organization.
But it’s a challenging endeavor that takes time to master. And since it’s closely related to the culture of every individual company, professional project managers have to understand the driving factors moving a company further, applying them to the day-to-day priorities for their staff.
The Ideal Scenario
Your boss (senior manager or the C-suite in smaller companies) is reasonable, passionate, open to adopting better workflows, caring, a hard worker, and a prolific industry expert. He’d discuss the process of landing new projects and assembling the workforce, too.
The project is, more or less, on track. Sure, a project that runs itself alone doesn’t need a manager, but you probably don’t want to start with a gig that’s 6 months behind and due next month.
The team is motivated, capable of executing, eager to learn and solve problems.
Clients are just fine. Everyone wants results ASAP and looks for shortcuts. But there are certain extremes you’d like to avoid.
Ideal scenarios rarely exist.
Businesses operate with limited resources. Senior management would love to close strategic long-term clients that require little maintenance and hire the most productive people out there sticking around for a decade.
But the dynamic business landscape is competitive, retention rates are low, salary requirements keep hiking, and operating a business is far from trivial when sitting on the top.
Management In Real Life
It’s worth noting that the management discipline is integral across companies in different industries where employee count varies from 5 people to tens of thousands of employees. Add different workflows and internal processes to the equation and you end up with a large variety of skills (or approaches) that apply to different organizations.
For instance, we’ve just completed a 3-month trial with a project manager coming from a completely different industry. She couldn’t adjust and become effective in our team - and we had to part ways.
After posting a new job, we’ve received 150 applications in a week. 40% of them were traditional PMs with PMI/PMP or PRINCE2 certificates used to work in enterprise organizations, slow-paced environments, 3-6 month-long sprints and various decision-makers.
We’re much more agile and those profiles aren’t a good fit for our team of 30+ which works in a more dynamic and fast-paced way.
Requirements for project managers vary. Some companies hire for a single product or an enterprise-grade project, usually in high-profile organizations dealing with tons of politics. Smaller startups and agencies often require managers to handle a dozen projects (or more), which relies on impeccable time management skills and keeping a close eye on scope creep.
Difficulties in Managing New Projects
Joining a new company and managing new and complex projects comes with its own list of horrors. Here are some of them:
1. Dealing With a New Company Structure
Companies tend to organize their structure in one of three popular ways:
- Functional organizational structure
- Project-based organizational structure
- Matrix organizational structure
Each approach determines the role of the PM in the organization and their day-to-day activities.
Which could span across several different areas as well.
If we take Henri Fayol’s techniques into account (who authored the 14 principles of management), the core areas a project manager focuses on are:
- Planning
- Organizing
- Leadership
- Coordinating
- Controlling
The amount of time a PM spends on each activity depends on the stage of the project, the maturity of the company, and the rest of the team.
Even if you’ve spent a decade in project management, it may still take you a few months to adapt to the new workflow. Workplace dynamics evolve with every single client or hire.
Discussing day-to-day priorities, along with long-term goals, is a great first step to kicking your first week off and setting your own targets for the job.
2. Building a New Effective Workflow
A project manager may be in charge of defining business processes, sparking motivation within the team, handling conflicts within the organization, overcoming objections indicated by product owners, writing project documentation, facilitating discussions between different members of the organization.
This also includes reporting, coordinating workflow with senior management, allocating resources for each sprint/interaction, identifying key players for a project - and often juggling multiple projects at once.
When you think about it, there’s a lot of “organizational” and “coordination” work which isn’t directly tied to a specific project. Building the right organization and creating the right workflow is paramount for other ongoing and future projects within the company.
This is why a PM may be less involved in a project’s day-to-day activities as they tackle other strategic areas of the business development process.
3. Leading a New Team of Different Personalities
From my perspective, it’s a fine start - it means there will be some obvious problems to start with. There are low-hanging fruits, too, and improving the team efficiency and productivity is a no-brainer (minimal effort in the right direction will get some decent results).
Of course, this usually means a ton of work and having to break some eggs for an omelet. Toxic people will need to go away. Interpersonal conflicts should be put to an end. Slacking has to be limited to a great extent.
You will make some enemies along the way — it’s inevitable if you’re leading the change. There’s no way around it unless you quit and try to find a friendly and positive place in a well-funded startup where everything goes according to plan.
And yet, you can’t kick this off as a new hire on the team. You have to study all stakeholders closely and align them with the rest of the organization.
We’ve designed a project matrix comparing projects’ complexity, effort, types of clients, the regularity of emergencies and more.
Organizations often have examples they rely upon in terms of extremes, i.e. “the best project” and “the most challenging one”. They come in different flavors, i.e. challenging projects often pay the most but take a toll on the team. Find out where you stand and how to improve the managerial workflow for maximum efficiency.
4. Setting up Priorities
One of the crucial questions to answer in a project management role is:
Who do I serve?
Since you can’t please everyone, you need a specific purpose:
- Your CEO/direct manager
- Your staff
- Or your own reputation
- The revenue (or your commission or something)
- The purpose of the organization
- Investors or board members
- Some 3rd party partners/peers
Most people would pick senior management or cash. That’s not the only choice so pick wisely.
Once you know the answer, find out what the action plan is. Create a SWOT analysis of the business plan, your team, the financials, projects, or anything else you’ve got in place.
In case some contracts are more profitable and fruitful than others, put more resources there. If some employees show tons of potential, promote them or give them some authority over the toxic staff.
That assumes you can assess the situation properly in a limited amount of time.
Then, turn the page and find out what needs to go away. People, projects, processes, tools.
Design a sample plan and present it to your manager after observing the dynamics for a few weeks. Managing projects is challenging, but improving the workflow takes time and multiple iterations. Continuous improvement is the key (compared to making rash decisions).
5. Plan The Long-Term Priorities
Once you’ve designed the short-term goals and targets for the company, consider the long-term priorities as well.
Chief Marketing Officers are notorious for their low retention rates. Organizations often don’t have clear requirements and enough patience to nurture CMOs, especially when they come from a CMO role in a different organization.
The reason is simple. Chief marketers have to prove themselves in the short term, nearing several months, while maintaining a solid track record in the long run.
This is extremely complex though. As discussed earlier, short-term goals often require cuts or changing business dynamics. This often has a positive effect in the long run, but the only way to pursue this is by hiring new talented staff or migrating to new software solutions (which requires training, onboarding, and gathering new data).
On the other end, you can use some ducktape and improve the short-term results, but the change would be temporary. It won’t last the test of time and the hotfixes will implode soon enough.
If this is your first time as a manager, this may be a hard problem to battle. And of course, CMOs are veterans in their space and rely on decades of practical know-how they can leverage.
But success and long-term growth in complex management require some experience in office politics, business development and growth strategy, finances, business processes in the industry, and then some. If this is outside of your comfort zone, it would be wiser to refuse the role and find something easier for starters.
Otherwise, it’s still a risky move but one worth pursuing. On the bright side, given proper leadership sitting on top, you may be looking at a VP role or even a C-Suite position a couple of years from now.
Your takeaway here is the misalignment between short-term goals and long-term growth. To accelerate, you need to stop or take a step back and jump. Long-term growth requires some delay and restructuring in the long run. Coordinate this with your senior management and find the best balance that works for the company.
6. Dealing With Crappy Scenarios
Your boss is clueless. Senior management decisions are poorly planned and executed.
The project is a mess. You’ve entered a minefield with poor industry practices and ridiculous execution, delayed time frames, false promises.
The team is cherry-picked from “The Office”. You end up with demotivated, poor performers, assigned to the wrong roles, who couldn’t care less about the company or the project.
The client is demanding, cheap, and had been promised the world.
Now, you can try to do miracles in leading the complex project but the outcome would likely be negative.
Of course, you don’t have to give up. Think objectively and list down the three critical priorities you have to focus on. The difficulty in managing complex projects lies in identifying the right priorities and finding alternatives that work for the organization.
- Is there a more experienced team member you can bring in without jeopardizing other projects?
- Are staff members more comfortable in different roles instead?
- Can you simplify the day-to-day workflow and streamline the operations?
- Can you discuss a couple of weeks in restructuring, cleaning technical debt, or improving processes with your client?
You can still handle the project successfully with enough perseverance in the right direction.
7. Scheduling Technical Adjustments
When we hired our VP of Engineering, he came up with some sensible (and legit) improvements to the technical process which we couldn’t enforce earlier. His tactic differed from ours in several different ways, the two I can name are:
- Introducing a new motto for the dev team being “stressless environment”, meaning that all of our processes aim for calmness of mind, limited overtime or late-night emergencies whatever the reason.
- Gamifying penalties by teaching a lesson without causing far too much stress. For instance, he never drinks alcohol yet he charges a bottle of whiskey and stacks these on his desk, as a badge of honor and a firm reminder of the future.
In another aspect, our deployment process wasn’t streamlined enough. We ran a couple of revisions of our git workflow and found some ways to work around longer deploy cycles.
Also, he built our Deployer Bot and introduced a daily process of signalling a deploy in the morning, scheduling a time, preparing task links and a pull request, and assigning a code review to the senior tech leadership.
Needless to say, this was convoluted at first, but failing to request that led to some unpleasant bugs missed by the QA team or merged branches which weren’t properly structured.
After some back and forth (and a quantifiable comparison), teammates started utilizing the deployer bot and enjoyed the painless process of launching with calmness of mind (with a couple of safety nets after pushing their PR).
Difficult Projects Can Evolve
The bottom line is that you must convince your crew that those best practices are not a bureaucratic overhead that they’re used to but actually bring value to the team. Use practical examples, tasks, pull requests, commits, business scenarios, customer requests.
Make it valuable: Show your team how best practices (clear docs, code reviews) save time, reduce errors, and lead to happier clients.
Start small, win fast: Focus on a few key practices and celebrate their impact.
Work together: Get buy-in from team and management. Be open to questions and tailor practices to address challenges.
Initial effort, long-term gain: Extra communication upfront leads to a smoother workflow, happier team, and higher quality work.
It may take a few turns but gradually, the team will agree to give this a shot.
Work closely with both your team and your senior management for optimal results. Communication overhead is required at first while you get adjusted to the flow. Bounce ideas back and forth and find the ones worth pursuing.
Managing projects is difficult. But the joy derived from turning a project around into a successful collaboration is worth the hassle.
