Effective Tech Leaders, Anticipate The Need

Jim Mortensen
April 18, 2023

What if you could anticipate every problem, issue or obstacle in life before they occurred? You might not be able to avoid them, but you could at least plan and prepare for them, better mitigating the consequences.

While it’s clearly not possible to anticipate everything in life, it’s an effective leadership skill to be capable of anticipating more than most.

The best leaders are forward-thinking and have the ability to anticipate the needs of their organization well in advance.

David Tucker II, President and Lead Developer of Clip Software, insightfully wrote that “as a leader, your job is to be the chief ‘need anticipator.’”

Anticipate and Solve Problems

7 Traits of Super-Productive People from the Harvard Business Review identified “Anticipate and solve problems.” as one of the key traits.

“The most productive people are great problem-solvers. They come up with innovative solutions and accomplish work more efficiently. They also tend to anticipate roadblocks and begin working on solutions in advance, and so avoid some of the problems that other people run into.

“But how do you do that?” you might ask.

No Crystal Ball Needed

When you think of “anticipating” you may equate it to being able to “foresee”, having “intuition” or having a “6th sense.”

Short of having a crystal ball, anticipating a future need may seem difficult or impossible.

While some might show an innate intuition, anticipating the need is a learnable skill.

The Merriam-Webster dictionary defines “anticipate.”

1: to give advance thought, discussion, or treatment to

It really is that simple. You anticipate the need by learning to give advance thought to something. Surprisingly, many people don’t regularly do this.

How many meetings have you been to where attendees are seemingly unprepared to discuss the topic or fail to read the relevant documents sent out prior to the meeting, let alone give advance thought to where the meeting topic and discussion might lead.

Besides giving advance thought, let me provide a few other tips for learning to anticipate the need.

Pay Careful Attention

When I was younger, my dad would ask me to help him with auto maintenance and repairs. I clearly remember the multiple times he rebuilt the air-cooled engine of our Volkswagen “bus”, which seemed to blow up every 50,000 miles.

I was more interested in programmable calculators and computers than auto mechanics. I frequently didn’t pay careful attention to what my dad was doing as I “helped” him work on our vehicles. I wasn’t a very good mechanics assistant – I rarely anticipated the tool or part he needed next.

To be an effective CTO you need to pay careful attention to the CEO – what he or she says, how she says it, what she does and how she thinks.

CEO’s usually think quite differently from a CTO. Giving advance thought to figure out what he or she is going to need will make you stand out from the crowd. Anticipate that need and get it done before they need it!

That will cement your relationship and turn you into a highly valuable, high impact c-suite colleague.

In addition, give advance thought to anticipate the needs of your direct reports. What are they going to need to be successful in their roles? Anticipate their individual strengths and weaknesses and what training, tools and support they might need, in advance of them having to ask for it.

Again, if we’re looking at what makes a high impact CTO, it’s not just about anticipating the future needs, it’s about anticipating what changes, tools and support those around you might need. Always be thinking a few steps ahead.

Learn from Past Experiences

History often repeats itself. Learning from past mistakes is critical to success as a leader.

One of my favorite movies is Groundhog Day with Bill Murray, where he relives the same day over and over and over again a 1,000 times.

At first, he isn’t paying careful attention and makes the same mistakes repeatedly as he relives the same day over and over again.

Eventually, he starts to pay careful attention and uses his repeated experiences to avoid mistakes and be at the right place, at the right time with the right help – he starts anticipating the needs of others.

His co-workers and the community become amazed at his “god-like” abilities to anticipate everything. At one point he supposes that “Maybe God isn’t omnipotent. Maybe he’s just been around so long, he knows everything.”

Past experiences help you anticipate future needs, but only if you pay careful attention and learn from these experiences.

A Hypothetical Mindset

In an Inc. article titled “How to Solve Problems at Work Before They Happen”, John Boitnott  provides additional insight on how to give advance thought in order to anticipate the need.

“One of the best ways to train to be more proactive with problem solving is to start thinking in hypotheticals. Try to imagine the possible outcomes of any particular decision, and think about potential snags that might ensue from it. Effective anticipation is going to rely on your ability to analyze what you know and apply it to what could happen. No one can accurately predict the future, but in the business world, things are a bit more predictable as long as you take the time to carefully assess known variables and apply past lessons.”

Preparing disaster recovery plans and conducting subsequent tabletop exercises is an example of how thinking in hypotheticals (i.e., what could go wrong?) and being proactive in preparing for a potential disaster helps you to anticipate technical needs (or potential needs).

The Parable of the Oranges

In summary, a good example of anticipating the need is shown in the simple story known as The Parable of the Oranges.

There was a young man who had ambitions to work for a company because it paid very well and was very prestigious. He prepared his résumé and had several interviews. Eventually, he was given an entry-level position. Then he turned his ambition to his next goal—a supervisor position that would afford him even greater prestige and more pay. So he completed the tasks he was given. He came in early some mornings and stayed late so the boss would see him putting in long hours.

After five years a supervisor position became available. But, to the young man’s great dismay, another employee, who had only worked for the company for six months, was given the promotion. The young man was very angry, and he went to his boss and demanded an explanation.

The wise boss said, “Before I answer your questions, would you do a favor for me?”

“Yes, sure,” said the employee.

“Would you go to the store and buy some oranges? My wife needs them.”

The young man agreed and went to the store. When he returned, the boss asked, “What kind of oranges did you buy?”

“I don’t know,” the young man answered. “You just said to buy oranges, and these are oranges. Here they are.”

“How much did they cost?” the boss asked.

“Well, I’m not sure,” was the reply. “You gave me $30. Here is your receipt, and here is your change.”

“Thank you,” said the boss. “Now, please have a seat and pay careful attention.”

Then the boss called in the employee who had received the promotion and asked him to do the same job. He readily agreed and went to the store.

When he returned, the boss asked, “What kind of oranges did you buy?”

“Well,” he replied, “the store had many varieties—there were navel oranges, Valencia oranges, blood oranges, tangerines, and many others, and I didn’t know which kind to buy. But I remembered you said your wife needed the oranges, so I called her. She said she was having a party and that she was going to make orange juice. So I asked the grocer which of all these oranges would make the best orange juice. He said the Valencia orange was full of very sweet juice, so that’s what I bought. I dropped them by your home on my way back to the office. Your wife was very pleased.”

“How much did they cost?” the boss asked.

“Well, that was another problem. I didn’t know how many to buy, so I once again called your wife and asked her how many guests she was expecting. She said 20. I asked the grocer how many oranges would be needed to make juice for 20 people, and it was a lot. So, I asked the grocer if he could give me a quantity discount, and he did! These oranges normally cost 75 cents each, but I paid only 50 cents. Here is your change and the receipt.”

The boss smiled and said, “Thank you; you may go.”

He looked over at the young man who had been watching. The young man stood up, slumped his shoulders and said, “I see what you mean,” as he walked dejectedly out of the office.

So, what does this story have to do with anticipating the need?

The employee who received the promotion didn’t need a crystal ball or “6th sense” to anticipate his bosses needs. He just paid careful attention to the original request, thought hypothetically and was proactive.

The employee anticipated the actual need without being explicitly told by his boss what that need was (i.e., to make orange juice for 20 people coming to a party). The employee bought the right amount of the right type of oranges and delivered them to the right place.

His boss didn’t even know what the actual need was or failed to communicate it to the employee. Just like real life.

Learning how to anticipate the need is a matter of paying careful attention, learning from past experiences, developing a hypothetical mindset and, most importantly, giving yourself space to give advance thought to what lies ahead.

Being an effective CTO is about your ability to become a forward-thinking leader and anticipating the need will help those around you work on solutions in advance and avoid the problems that others run into. No crystal ball needed!

About the Author

Jim Mortensen is a fractional CTO, COO and technology leadership coach based in New Mexico.

He is an experienced tech leader with extensive business achievements over a wide range of domains, with expertise in integrated justice information systems, payment card industry, AWS Cloud, and data security.

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