Startup project management strategies: how to maintain morale while kicking a$$

I have worked predominantly in startups or SMBs and the perks are quite amazing. I get to listen to music at work with my noise-canceling headphones plugged in (yes, even that is amazing). The culture is slightly more relaxing, where ideas are allowed to flow during brainstorming sessions. However, when things get too comfortable, you will lie in the valley-of-death…forever. Yikes.

In our previous posts, we have talked about ICPs and how CRM tools can help streamline processes. However, managing a successful project takes zest, strategy, and management.

Flexibility

I think the beauty of a startup is its flexibility to adapt to changes. A smaller team allows for easier communication and taking a shift does not require extensive amounts of effort. It is still horrible, but you won’t have to face 100 disgruntled employees from 5 departments.

However, flexibility when left uncontrolled, can create messes. Pivoting without proper management or strategies will lead to drowning.

I like looking at numbers, so let’s look at some:

1. Around 65% of projects that are not done with proper strategy management are likely to fail.
2. 11.5% of time and monetary resources are lost due to unwanted mistakes from improper management.

He spent $10k on the domain

In Brooklyn 99, they had a perfect bone broth project that could help people recover from muscle aches. However, poor project management eventually led to failure, broth explosion, and a ton of money wasted.

Here are some tips for startups when dealing with your newest project.

Realistic Goals

It’s December 2023– have you achieved the resolution that you set at the beginning of the year? It is quite likely, as I hypothesize, that huge goals like losing 10kg within 4 months would be more unattainable, as compared to streamlining your dieting process: “Maybe I should go to the gym twice a week in January and thrice a week in February”.

Just as what it is like in a business, 1000 customers sounds like a horrifying amount of work but setting measurable goals would allow you to see actual progression.

Good goals can follow this model: Specific, Measurable, Achievable, and Timely (SMART).

1. What are some specific plans you would set in the next 3, 6, and 12 months?
2. How would they be measured?
3. Are they achievable?
4. What are the deadlines for each segment of your plan?

Additionally, SMART model should also consider the efficiency and ability of your team members:

1. Are your members well-trained?
2. How high is their morale?
3. Would they need additional training or assistance?
4. Would readjusting the goal increase the probability of success?
5. How open are they to changes?

Milestones

I am a highly competitive person and I would not rest till I get what I want; however, as I overestimate my abilities, I crash– hard.

Setting milestones would allow the team to track progression more efficiently; many tools in the market are created to serve that purpose (eg. Monday.com, Trello, Teams, Calendly, Hubspot, Salesforce, etc.). However, the more CRM tools one uses, the daunting pressure of a screaming deadline and just keeping it updated is already tiring.

Hitting milestones should not be that difficult. For example, WTS is created to streamline and hit milestones. I am a procrastinator and using one platform allows me to focus on the task at hand.

Prioritize

‘Duh’ of course. However, prioritization is not everyone’s forte, especially when everything seems like a top priority. Here are some of the tips I have learned:

1. Complete the easiest tasks first when you clock in to work. I love starting work feeling like I’ve accomplished something.
2. Prioritize specific details of a larger plan
3. If you can’t solve it now, set a deadline– the ideas will flow when you stop chasing them.
4. Set a deadline, otherwise your priorities will never be fulfilled.

Communicate

Everyone can speak, but not everyone is an effective communicator.

I used to write reports for a human rights organization (name, redacted). My supervisor just dropped the assignment, without providing me with a template. I assumed it was like a thesis, but lo and behold, I messed it up. Instead of telling me what to do, he sighed, and said “Never mind”. I asked him for a template again and I completed it within 30 minutes.

He was a poor communicator, but I was no better.

Present day, my bosses communicate their expectations clearly to me and I have the autonomy to set my targets. Each conversation took an hour or longer, but everyone was on the same page and the results were visible.

Good communication increases productivity.

In conclusion, startups are fun but it takes a ton of work. With the right project management strategies, success will be closer than you think.