“Measure twice, cut once,” counsels the old adage. My grandfather would recite this to us often, as he cautioned us to assess well before acting on an idea.

Expanding on this, I would say that good planning is the key to making things go right.

Whether your goals are financial or otherwise, defining how you will go about achieving what you want creates a roadmap to keep you on track. This will help you to assess how things are working along the way, and to course-correct in case of need so that you arrive at your desired destination.

But a map is only as good as its accuracy. It must identify up-to-date and relevant information, best roads and ways, and cautionary twists and turns. How do you develop yours so that it works well?

The following five considerations serve as a useful guide.

Do you know your end goal – and is it yours?

Having a clearly-defined “destination” in mind is key. Be very specific. For example, if you want to retire in 5 years, what will your life be like? What kind of funds will you need to support the lifestyle you anticipate? How can you plan for the unexpected (or can you?!).

What other questions should you be asking yourself? Checking with a good financial planner will alleviate guesswork and set you up for success.

Further, is the goal you are setting truly yours? Or is it someone else’s priority?

I once talked with a couple who expressed the desire to move closer to their kids. Over the years, I noticed they talked quite a bit about it but never took the plunge. After some time, the husband would make cutting remarks about the wife not making any decisions toward moving.

Finally, she confessed that she really did not want to relocate. She felt that her friend circle was important to her and that if they moved to be near the kids, they risked the kids relocating at some point in their careers.

This happens quite often – someone agrees with someone else’s goal when they haven’t really evaluated how important it is to them. If you are in this situation, do yourself a favor (and the others involved) and have a tough, frank conversation. You’ll save a lot of poor feelings that will otherwise build up over time.

Who should be involved in the planning and the decision-making?

Have you ever been surprised to learn that someone else has planned something important that impacts you – but you were not consulted? Remember this as you do your own strategizing.

Who has impacted your goal? Who should be part of the planning process because of this? Be candid with yourself and if you find you procrastinate about including them, ask yourself what you fear most.

Do you fear that they will not support the goal? Or that they will want to reach it a different way? Again, those conversations can be challenging at times but then so are relationships, in general. Negotiating a win-win is necessary if you are in a high-stakes relationship that is impacted by the future you want.

Ask the right questions.

When I work with CEOs and their teams, I find quite often that they are not asking the right questions in order to meet their goals.

For example, one executive team operated off the premise that the way they had done things in the past would work for a future initiative they wanted to undertake. This assumption was false, and they had to do a lot of repair work which cost time and money.

Ask yourself and the other decision-makers involved in your planning what questions you need to ask in order to avoid missing opportunities. Note any language, such as, “We can’t, because…” or “That hasn’t worked in the past…”

Shift your limited thinking by asking, “How can it work…”” rather than, “It won’t work.” You’ll be surprised at the possibilities that lay beyond.

Use your values and priorities as your guard rails.

What is important to you must be respected.

For example, if you feel that the children from your blended family should all be treated equally, then remember that as you do your estate planning. If your values include family, be sure that in your financial planning that you build a healthy budget for visiting them, when desired.

Set deadlines and monitor progress.

It’s always a good idea to pause and assess whether the plan is getting you where you want to go.

How do you do that? Identify success markers – incremental signs that things are working. It is devastating to work on a plan for years, only to find out it isn’t working. You should never find yourself in that situation.

Instead, note what you need to see along the way that tells you that you are still on the right road. And again, check with the appropriate professional if you are not clear on this. Any good navigator has a team to support them so that the journey is more enjoyable, and success is met.

Are you confident with your roadmap? Will it help you reach your goals? If you feel stalled or you don’t know where to begin, be sure and consult the right professionals for support. Just as any navigator has their team, so should you, so that you arrive at your destination safely.

Patti Cotton serves as a thought partner to CEOs to help manage complexity and change. Reach her by email at [email protected].

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