5 questions you should ask before starting a project

By Sedora Tantraphol

Here at Moonsail North, we love the opportunity to serve as thought-partners to clients who are on the critical cusp of launching a new product, program or project and need guidance. That guidance might involve determining whether it’s feasible to begin with, the right time to push forward, a good investment, and sustainable.

Whether you’re considering starting up an initiative, launching a new fundraising event or pursuing a side gig, we recommend going through this exercise as part of your due diligence in answering the all-important question: “Should I do this (now)?”

1. Is there a there, there?

This one seems so simple, yet is often overlooked. Typically, what happens is an organization’s staff or board gets carried away with the idea of a new unicorn, without taking the time to reflect deeply on whether there’s actual substance.

A nonprofit scenario: A good example is seeing a sizable grant opportunity for a project that kind of fits with your work, and wanting to submit a grant proposal because you need to fund your staff’s salary one way or another. Key questions include:

  • Will getting this grant cause mission creep for our organization and take our staff energy away from our core programs?
  • Do we have a concrete, detailed plan?
  • Do we have a curriculum?
  • Do we have the right networks and expertise?
  • Is there another outfit in our geographic footprint who does this better than we do?

After you ask the hard questions, you may figure out — after hours of meetings, research, maybe even some initial proposal drafts — there just isn’t a there, there. That is not time and effort wasted — better to find a new direction than to pursue one that will not yield results.

A small business scenario: For small businesses, what this often looks like is doing too much, too soon. You see what others are doing, and want to do it too. But, it’s important to stay focused on your core areas of expertise / core products and not stretch yourself too thin. If pursuing this new line of business is going to take your attention away from what’s working, you shouldn’t do it. You need to really develop it and put in the sweat equity of lining everything up — from branding to messaging to marketing to financing.

The fix: Before getting too far ahead, have an initial exploration meeting with your team (or, if you work alone, find a consultant) to really flesh out the details and figure out honestly if there’s a there there.

2. What’s my capacity / our team’s capacity?

It can be hard to balance your optimism and excitement to launch a new product or program — because you know the community really needs it or because you know the market is hot — with the reality of how much time and energy it will take.

The fix: Have an honest discussion with yourself and your staff about how much time this project will need, and how much time you really have to dedicate to it. You need to consider what else is coming down the pike (maybe your work is seasonal, and you’re struck with a good idea right now, but you’ll be tied up during critical points later on). It’s absolutely critical to know your limits and say no to projects until you can dedicate a consistent amount of time to it without burning out.

3. What resources and experts will I need?

This is connected to substance and capacity issues. It’s important to consider the full range of resources and experts you’ll need for the project to be successful, and whether you can realistically secure all of them in a timely manner. A well-rounded team could include the following and many more:

  • legal counsel
  • accountants and bookkeepers
  • real estate agents
  • loan officers and others in the financial sector
  • staffing and human resource consultants
  • communications consultants
  • consultants who will handle strategic planning and capacity building
  • specialists with knowledge of specific issue areas foundational to your endeavor

The fix: Do your due diligence to determine if you can actually secure everything and everyone that you need. If not, it’s probably better to put this on hold for now and find a way to extend the runway so you have an easier time pulling it all together. Prioritize. Tactics include speaking with others who have gone through this, getting quotes, and getting your spreadsheets going to  conduct the necessary calculations. Group-based resources include associations for your sector and local business groups (such as local chambers of commerce) — but if you can budget for it, there is nothing better than a consultant who can focus on your specific needs.

4. Will this bring joy into my life? (Or, is there a good ROI?)

This one can be hard to predict, but it’s important. Start by asking yourself if doing this day in, day out will bring you joy. Does it connect with your passion? Will you be proud to do it for a long time? If you are investing a lot of resources into it, will there be a good return on investment, in terms of name recognition/results/clients/profit?

The fix: If the answer is no, keep looking. There is nothing easy about launching a new business or scaling up, and if you have the option to determine your path, you will want to find a better fit. (If you are a staffer with a directive to determine the feasibility of a project, that is another story.)

5. What might be some pain points, and how can we problem-solve them?

Pain points are things that you hate to do; you may literally prefer to do 18 other items on your to-do list first. You might have emotional avoidance around them. For some people, it’s setting prices or doing invoices and following up on outstanding payments. For others, it’s starting the first draft. For still others, it’s using Excel or working alone or having to play the role of marketer. Whatever it is, it’s important to identify your pain points — and those of your teammates — before going into the project, so that you can problem-solve the issue to ensure a smooth workflow process. Trust me, there will always be someone else, especially in the form of a consultant, who enjoys the thing that you will avoid doing.

The fix: List out your pain points. (Hint, this is what you always procrastinate on.) If you’re doing this as a team, have everyone list out their pain points. Next, go through each pain point and see if someone else on the team is willing to take it on. If not, consider creative ways to outsource the task so you don’t have to do it. This will lead to everyone on the team feeling more energized, and working more efficiently and effectively.

If you’ve gone through this list and want someone to talk through your ideas and concerns with, contact us — we love doing micro-consultations to help you figure out what’s right for you.