3 Other Useful Skills for Strategic Thinking 

Strategic thinking is critical when prioritizing and de-prioritizing, and we just discussed some skills. But there are many related skills you will find useful in work and in life. As you work to prioritize stuff and to-dos in your life, here are some other skills you will draw upon: 

1. Delegation – Some people love to delegate, while others find it challenging. The old saying goes, “If you want it done right, do it yourself.” If you’re used to having things done a specific way, you may fear delegating to others — whether it’s something at work or cleaning the bathroom. The other hurdle with delegation is that it often requires some of your time at the start: explaining the tasks, training, answering questions. Then, when the task is done, you must follow-up to check the work was done correctly. While this initial time investment is tedious, delegation is a critical way of getting more done and feeling less overwhelmed. Here’s how to get started: 

• Start by delegating tasks that are easy, so that explaining them and checking the work won’t take as much time. Which tasks could be easily assigned to someone else? 
• Which tasks do you dislike? Those are going to feel easiest to delegate and you may find someone who likes doing those things. Delegating them will prevent you from procrastinating. 
• Consider also what items take a long time. Can part of the task be assigned to someone else?  
• Depending on your role at work, which tasks should you delegate because your time is better spent elsewhere? Sometimes there are things we like to do, but it’s smarter business to assign those elsewhere.  
• Outline in a document what you expect with this task or item. What does a successfully completed task look like? What should the person know about it? You want to set him/her up for success, not failure.
• Schedule some time to manage delegation, for the initial assignment and then for following up.
• Be open to questions and to new ideas. He or she may have a different way of getting it done. If the result is good, don’t get hung up on the process.  
• Over time, if you delegate the task to the same person, he or she will learn well enough what you expect and you won’t have to check on it.  

At home, you can delegate some chores. Your children, partner, or roommate can all pitch in on cleaning. In this case, if it’s not done exactly the way you want, you might need to live with it. After all, a clean bathroom not quite perfect is better than a dirty one! You could also delegate the cooking, even if it’s just one day per week.  

On your nonprofit board or volunteer commitment, delegation might look more like saying “no” to some items. Or, you can ask for help with a project you’re doing. 

At work, how and what you delegate depends on your role and assignments. If necessary, speak to your boss about your workload. 

2. Decision-Making – When you have a lot of choices — or if you don’t like your choices — making decisions isn’t easy. We often worry about the opportunity cost — the thing we’re missing out on by choosing Door A instead of Door B. What if we choose wrong? What if the choice goes sideways and people blame us? But sitting on the fence is just as bad. Over time, not making a decision is a decision in itself: letting things happen to you instead of taking some amount of control.

Often in tough decisions, we know what we need to do, we just don’t want to do it. In that case, take a deep breath. You might also write the pros and cons to help yourself see that it really is the smart move, even if it’s unpleasant in some way. One person we know did this when deciding whether to send her child to kindergarten this year or to hold him back in preschool. None of the choices felt great, but she broke down all the options and weighed the pros and cons to help make the right choice for her family. 

 The other thing about making decisions is that it becomes easier with practice. Of course you can decide between chocolate and vanilla ice cream, but it’s far scarier to pursue a new career path versus staying comfortable in your current job. Still, every time you make a big decision, you get a feel for it. Over time, it will become easier. 

 Can’t make a decision? 

• Ask yourself – why am I having trouble with this? Is it that I just don’t like my choices? 
• Is there something I don’t understand that’s preventing me from making the decision? If so, how can I get more information on that? 
• Am I waiting on someone else’s input? If so, why? Can I make the decision without it? 
• Try a pro/con list. Does that help? 
• Or, you might try giving each option a weight and totaling them up. 
• Another option is to write freely, write down all your random thoughts in a notebook. Don’t bother with organizing them (unless you want to) — just free flow write all the thoughts that pop into your head about the decision, what’s blocking you, what you hate about it, what the benefits are once you’ve made the choice, anything. At the end, you may have it figured out. But if not, you may at least feel better. You can also sit on it for a day and re-read what you wrote for greater clarity. 

3. Time Estimation – Time is a strange thing. That boring meeting you attend seems to last forever, while that fun weekend with your partner felt too short. That’s why estimating time is such a challenge; we can’t really grasp it. Studies show the older we get, the faster time seems to us.  Most of us aren’t accurate at estimating time. (Or we overestimate our ability!) Here are some ways to get better:

• Use this time sleuth sheet this week and take a look at your activities. Try this for two full days or even a week if you can. You’ll start to see which tasks take far longer than you expect. 
• Plan out your day. Use these Shoe Cubby charts (personal and professional life) to help you realize how many hours you actually have for free time. Don’t forget to include time you spend getting ready, driving, etc. 
• Always late? For one full week, bring a little notebook with you and write down every meeting or event start time. When you arrive, write down your arrival time next to the start time, followed by the difference. e.g., 8 minutes late, 6 minutes late, etc. For example:
  • Monday – 10 a.m. — 10:04 — 4 minutes 
  • Tuesday – 11:30 — 11:36 — 6 minutes 
• Once you get a full week in, take a look — are you always about the same amount of time late? What can you do to alleviate that?   
• Some people find it helpful to set an audio cue as they work. If you tend to end up in rabbit holes, distracted from your task, set a timer to ping every 10 minutes. When it chimes, ask yourself if you are doing the thing you are supposed to be doing. 

Do you need help with some of these skills? We can coach you through life’s transitions. Contact us for guidance.