Get Over the Thought that Engineers Are Being Difficult (When They Are Not)

Lee-Ling Yang
6 min readDec 29, 2020
Photo by nxvision by Unsplash

Some individuals don’t respond well with rules. Develop an understanding of why they react that way, you will realize that they do not intend to question or go against you.

People are motivated by one or a combination of:

- Inner expectations stem from themselves — commit to themselves

- Outer expectations come from others, work and society — commit to others

Four types of individuals arise as a result of this, defined by Gretchen Rubin, the author of “The Four Tendencies”.

4 types of engineers — based on wha

In my experience:

  • Engineers and designers are questioners. They need context to know the best way to solve problems.
  • QA are upholders. They need clear rules to know what a “working” feature means.

Take this into consideration when hiring and pairing engineers. Balancing out the team with diverse personalities can avoid conflicts and disagreements.


How do you know you are working with questioners?

  • They do what makes sense to them, even if it means defying their peers and bosses’ expectations.
  • Their favourite phrase is “why”, so they can rationalize whether they should do what’s being asked of them.

How to convince questioners to do things?

  • Be prepared to explain “why” you make a decision and “why” they are being asked to do certain things. With clear justifications with sound reasons to all their questions, you will earn their respect.f
  • Your explanations need to be logical “in their mind”. Document what they thought was “wrong” in the past. Understand what context they lack or what wrong perspectives do they hold if they disagree.
  • Few decisions are completely right (white) or wrong (black). Explain the uncertainties and factors that make it fall in between (gray). Convince them that the chances of being right are greater than wrong.
  • Frame it as an experiment to decide if it is the “right” thing to do. “Try it to find out if it works. If not, try something else.”

What to watch out for?

  • Don’t get defensive if they ask “why” — even if it feels exhausting having to convince them.
  • Their desire to justify decisions can mean taking a long time to conduct research and analyze the pros and cons. Ask them to “timebox” their effort on research when it comes to open-ended questions with a vague scope. Alternatively, ask them to compare the pros and cons of going with a limited set of options.
  • Ironically, they get impatient when being asked to explain their reasoning. They become over-confident after their thorough research and can’t comprehend why others think they can be wrong. Instead of saying “why are you doing that?”, try expressing curiosity by asking “How did you come to this conclusion?”

What tasks are best for questioners?

  • Consult them when you need to understand why an existing process or tool is chosen. They likely have rationalized the choices in the past. They will be happy to share since they take pride in their thorough thinking.
  • If you are a manager that needs honest opinions on your idea, run it by them because they are not afraid to speak their mind to authority.
  • Get them to drive change and push a plan forward, as long as they think it is the right thing to do.


How do you know you are working with rebels?

  • They enjoy being different. They dislike conforming to rules and like to go against what everyone else does — even if that means criticizing others.
  • They take pride in being true to themselves and enjoy sharing their strong beliefs.

How to convince rebels to do things?

  • Appeal to their beliefs and identities. Rather than arguing why they are wrong, build relationships by patiently listening to their opinions.
  • Use reverse psychology, as they want to prove you wrong. For example, “I bet you won’t do xyz”, “can’t you do better than that?”
  • Share what others think — so they can be different. For example, “Everyone thinks this is not fixable”

What to watch out for?

  • Come off as arrogant and not a team player.
  • The more you nudge them and prove them wrong, the more they resist. Give them time to come to their own conclusion and ask “what did you decide to do?”.
  • If you intend to establish clear processes and cannot afford a bad example, speak to them in advance.
  • Be careful when giving them recognition. They may feel they are tricked into doing it for someone else. This keeps them on guard and strengthens their desires to rebel in the future.

What tasks are best for rebels?

  • Given they are technically competent, they can tackle problems that most think are not possible.
  • Set up systems and processes that are in line with their values. They thrive on autonomy that allows them to shape the “world they believe in”.


How do you know you are working with obligers?

  • They struggle to keep up with the goals they set for themselves.
  • They will do things for someone else that they can’t do for themselves

How to convince obligers to do things?

  • Explain the significance and impact their commitments have on others. Give recognition and show appreciation for their contributions.
  • Hold them accountable by setting clear deadlines and deliverables. Make them aware of the consequences of missing the dates.

What to watch out for?

  • They are prone to burn out, as they fear letting people down. Even if they don’t enjoy the assignments, they will still take them — especially if the tasks are critical for the team.
  • Asking them to study new technology on their own or provide regular status updates can be a challenge. Pair them with self-starters to keep them in check.

What tasks are best for obligers?

  • They don’t view “boring” tasks as meaningless — as long as they know their efforts make others’ lives better.


How do you know you are working with upholders?

  • They turn anything into a to-do list, as they get fulfillment from getting things done and meeting their own goals.
  • They will follow rules and deliver what you expected on time with high quality — cause they made you the promises.

How to convince upholders to do things?

  • Set clear requirements and sprint goals. Write them out in the form of a checklist.
  • Assign them tasks that help advance their personal and professional goals.
  • Share the positive impacts their work has on others. Tell them how much you trust and believe in them.

What to watch out for?

  • Come off as a “micromanager” or “perfectionist”, as they expect others to have the same standards and do things the “right” way.
  • If people fall behind and things are unorganized, they get frustrated — especially if it causes them to miss goals and hurt their reputations.
  • Reject starting work with ambitious timelines and vague requirements. They fear missing targets that let others and themselves down.
  • Even if the goal is no longer worth pursuing, it is hard to drop it. They can perceive this action as “giving up” or “disappointing themselves”.

What tasks are best for upholders?

  • Give them projects with clear timelines. They can manage it with little supervision. They feel responsible to inform you if any risks can cause a missed deadline.
  • Set great examples for the team, if you want to implement new rules and processes.

Sum it up

It is tempting to shove something down someone’s throat and ask them to “just do it”. If they are not convinced, they would just do the bare minimum to deliver what you need.

To multiply your team’s productivity, task someone with what they are naturally good at. To them, it is like a reflex that doesn’t take much thinking and effort. This saves you time from training someone else to reach the same level of proficiency.

Strength can also be a weakness, depending on the context. Avoid giving them tasks that cause them grief. Watch carefully when teaming them up with the same personality type that causes conflict. Don’t take it personally if they sound defiant.

Building a high performing team is everyone’s job.

Want to work more effectively with engineers?

Check out these related articles:

Download my book How to work with Engineers

Link to get the book “How to Work with Engineers”



Lee-Ling Yang

Product @Microsoft Teams. Previously, Director of Product @LionDesk. Ex-Biologist. Training for my second Triathlon. Empower Women in Tech.