How to Build and Keep a Winning Technology Team

Definition of a Winning Technology Team

I want to share concepts and leadership styles that may help future leaders build and keep a winning team. All of these items are things I practiced and believe contributed to the success of my Team. Note that some teachings described here may not always apply. Take it with a grain of salt. Let us define first the benchmark what is Winning Technology Team in the field of Cloud Computing:

1. 4 Years of No Infrastructure Downtime

2. 0 Attrition over 3 years

3. Deploy to production in 5 minutes.

4. 0 Downtime Deployment

5. 0 Error Due to Configuration

6. Self Thought Engineers formal and informal

7. Self Certified Engineers

8. Immersion and On-boarding Program

9. Can Deploy 14X per day in production

10. Successfully navigated 4 technology black swans

11. Rated 98% Team Satisfactory Score[Pulse Survey]

12. 0 Infrastructure Rework / back job for 5 years

What makes a winning team? The members of this Winning Team described above are just like anyone else. They all consume 2 cups of rice, struggle to do 20 pushups, drink soda every afternoon, and eat the same $4 sandwich every day, just like everyone else.

What is it with Steve Balmer and Jeff Immelt? They both started in Procter and Gamble just like any other quintessential interns. Yet both turn out to be one of the few most successful leaders Microsoft and GE respectively. The answer is that winners are not born; they were created through deliberate practice(Talent's Are Overrated Book). This goes the same in building a winning technology team. Here are the lessons I've experienced Building a Winning Technology Team:

Lesson 1: A Mission and Vision So Clear are needed To Build and Keep a Winning Technology Team

It is essential to develop a captivating and motivating vision for one's team. This vision should be ambitious yet realistic. It should be easily communicated and remembered by all team members. The vision should be vivid and well-defined, enabling each member to envision the future. Ultimately, a leader must be contributor to a vision not someone who just wait making it happen. An inspiring team mission and vision will attract future talents during interviews and, at the same time, retain existing team members, knowing they are up for something great. Here are some strong examples of powerful visions:

1. To be Earth's most customer-centric company - Amazon

2. To inspire and nurture the human spirit. One person, one cup, and one neighborhood at a time - Starbucks.

In my Technology Team, we have 2 mission and vision statements. These statements are written inside the DNA of all members constitutional preamble. When confused, always go back to your mission and vision, there you will find the answer:

1. To build the most beautiful cloud infrastructure that helps businesses grow and flourish while nourishing our career.

2. To confidently ship codes to production reliably, fast, and easy so that people can sleep well at night.

Reminder: Your team mission and vision statement are not for a show. You must authentically live and breath by it.

Lesson 2: Culture and Skill are Non-Functional Requirement. Only Hire Class A Person

Class A attracts Class AAA, while Class B people attract Class C & D. Come up with a selection and interview framework. In my case, my selection framework can only be passed if you belong to the upper top 5% of the league. When hiring, you should do the Moneyball thing, look for complementing talents. Also, hire for a one-to-many function, meaning only hire a person who brings multiple specializations, e.g., a Cloud Engineer with Development Experience and DevOps is a gem. Not only will you save your organization a lot of money, but their variety of skills will produce limitless results just like 8 notes making beautiful chords.

Each time I form a team, applicants undergoes 5 interviews. The first two are culture fit-centered, where I work with Human Resources and my most senior member. They are tasked to cross-validate the personality of the applicant versus the company culture. The third and fourth interviews are technical. There will be a panel interview and one-on-one. After passing the fourth interview, I usually give a simplified case study of a day-to-day to simulate real world scenario. The applicants are asked to provide a solution to 3 technical case studies. The solution for case studies will be defended by the applicant to members of the team.

The intent of the case study learning approach is to see how well a person addresses real-life scenarios if we ever have to hire the applicant. I am looking for a practical solution; it does not always need to be right. I just want to see his reasoning skills, tenacity, creativity, and never-give-up attitude. Some may question my approach, but it resulted in "0 attrition for 3 years because we managed to get Class A that are self-motivating."

Usually I look for top 5 qualities in applicants:

1. Entrepreneurial

2. Calculated Risk Taker

3. Good Communicator (By no means I don't mean news caster style).

4. Integrity

5. Courage

I would borrow Simon Sinek's graph in choosing the best of the best. When choosing or keeping talents, one has to consider the correlation of trust and performance. Hire people who are high in trust and medium to high in performance. Avoid people who are high performers but low to medium in trust.

Reminder. Having a strict selection process does not mean hiring and onboarding will be slow. Work with Human Resource so that the process remain fast.

Lesson 3: Clarity and Follow Through

There are two types of leaders: a leader who just wants a result but cannot comprehend how to achieve it, and another leader who wants a result but is clear on the action plan needed to achieve the expected outcome. Consider the two scenarios below. Only leaders with follow-through can gain the respect, trust, and commanding presence of a Class AAA Team. Only headless chickens will follow Wishful Thinker Leaders, which is why they always end up falling short, no matter what.

Scenario 1: Burning House

Leader A: Wishful Thinker

One leader will say, "Stop the fire, stop the fire. You are a failure if you can't stop the fire. I said stop the fire. I don't see a reason you can't stop this house from burning."

Leader B: Follow Through Leader

Priority is your life. Along the way of the escape, save and bring as many men as you can. On your way out, get important documents as long as it does not hinder the escape plan. After we exit, we can then blast the house with water cannon; hopefully, we can still stop the fire. Remember, I will be with you the entire way.

Scenario 2: Build A Bridge

Leader A: Wishful Thinker, motion vs action.

I want you to build a bridge to connect two islands 1 KM apart. Tell me when can you finish it? Once done, let me know, this should be easy. Forget the plan, compliance, and building code, they can follow, I wana see "motion".

Leader B: Follow Through Leader

Let us build a bridge to connect two islands 1 KM apart. This is both strategic and historical. It is strategic because it will open trade and commerce for the two islands. It is historical because many had tried before but many had failed. I believe I have a secret sauce to connect them. We have the chance together to make history. The idea is building the bridge in many modular portions, and we will use a suspension bridge approach. You need to put into consideration the frequency that the wind will generate.

This is just a rough idea. Assemble a team of engineers and architects so that together we will create a plan that we can review many times. Part of the plan will be budget, engineering, and architectural considerations, most of all safety of builders and future people passing on the bridge. As long as you have viable plan, start immediately. I will provide all resources needed.

Reminder:

• Clarity and over communication builds a winning team. One of the reason Formula 1 winning team wins is their over communication and clarity of details during race.

• Plan even though invisible is an action itself, work out of plan is an action, work out of no plan is motion.

Lesson 4: Be Decisive and Risk Taker While Valuing Everyone's Opinion

To build a winning team, it will be very inspiring for engineers to see their boss being decisive. A decisive boss does not need 100% data availability to make a decision, a detailed foolproof plan, nor overwhelming evidence to make a decision. A leader must listen not only listen to popular decision but through objective wisdom. He must remind himself that the best decision comes from the 1% of population. There will never be complete data to come up with a decision; at most, 70% is enough to decide.

There will never be a perfect plan; a plan that is well thought out and well reviewed is enough. Changes along the way can be accommodated by a winning team. A leader must have the guts and courage to make unpopular decisions and should be willing to execute without having to get the opinion of everyone. The worst thing a leader can do is to follow a subordinate with the loudest voice or to resort to a voting decision approach. The fastest way to demotivate and make your winning team members leave is through indecisive leadership. Below is an example of how a decisive leader in technology reacts in a situation.

Engineer:

Hi Matt (The Leader), I just recently received a patch notification from our cloud provider at short notice. The notification requires us to patch 50 databases in RDS, including our critical infrastructure, which will entail downtime.

Leader:

Gather the team. Let us make a detailed plan. Since we are not familiar with this new patch and its behavior, we can then prioritize our RDS database Development Environment. Do not worry about breaking the Development Database; that is good news because we will be able to make a preemptive strike rather than breaking Production. During your patch to the Development Server, document everything as it will serve as validation for our plan. That's my recommendation. If any of you have a more efficient plan, please share. See you guys in 1 hour.

Remember: Decisive Leader is inspiring and contagious to your Team. They will likewise do the same. As they become decisive too, you are on your way of building a winning Team.

Lesson 5: Give your People a Purpose

To give people a purpose, let me borrow "Simon Sinek: Start With Why." Always explain, even every day, the purpose of each milestone and objectives to your team. Then, relate this purpose how their role plays an important part in making it happen. Borrowing Simon Sinek's example again.

Both ThinkPad and Apple can hire the finest engineers in the world, but what is it about Apple that they make more beautiful laptops? That is because, in a research conducted by Simon Sinek, Apple Computers overemphasize the purpose of the company and why the contribution of each employee matters to fulfill the goal. I do this with my team; each time we have critical work to do, I clearly state the "whys." Here are some examples:

"We need to exit from this technology in 6 weeks to save our company from vendor lock-in before this contracts renews in 2 months time. There is no turning back but be mindful that any mistake in our part may cause our job. which makes this even more exciting.... I need you to identify the connectivity of each app over the core systems so we can assess the impact to business on the day of cutover. I am counting on you to do this."

Remember; A Team Member or a Team without purpose will auto pilot to find their own purpose. As the leader; you may or you may not like the outcome of a self generated purpose out of boredom. Better to be the one making a purpose.

Lesson 6: Build A Circle of Safety

We are on it together. I've got your back, and you've got mine. That is how to build a circle of safety. Do not mistake this though for tolerating wrong doing or getting outside your core values. Think of your team as tribespeople; all of you hunt together in order to survive. As tribespeople hunting, one is tasked with driving the prey to the tribe, one is tasked with throwing a spear at the prey, another is tasked with throwing the net over the prey, while others are tasked with cooking the food.

One policy that I promote in my Cloud Technology Team is that "no one will ever get fired or reprimanded for any mistake big or small as long as they conducted the due diligence prior to doing the tasks and it has been done with proper caution, process, and judgement". I've seen countless times leaders tend to become "expert due to hindsight" but failed to do the foresight prior. As a result they seem to have known better.

A leader should have the I will be the first to get fired mentality. Take cloud migration as an example. Sometimes rollback is inevitable due to factors beyond human comprehension. If I my self will make the same mistake as others did, no one gets reprimanded.

Another example of mistake that should not be punished or reprimanded is a Kubernetes EKS upgrade is a quarterly activity of a hypothetical team. They have laid down a standard procedure for this activity. All members are capable of performing the upgrade for years. However, there was one instance where after the upgrade, the Kubernetes EKS cluster wouldn't start. Yet all standard procedures and steps had been conducted properly. It was later found out that the "master node certificate expired, coinciding with the upgrade." None of the team members should be punished as no one would have been able to predict such a scenario. Focus on creating counter measures, revising process, and fixing what is at your control in that moment rather than fault finder.

Reminder: If engineers and leaders feel safe with each other, their performance will go beyond expectation. Each member will be willing to make sacrifices.

Lesson 7: Be Authentic

Nothing is more demotivating to a technology team than a fake leader, meaning a leader who would pretend to be someone else. Technical teams are very intelligent beings; they would immediately recognize if you are faking or pretending to know something you don't in order to appear in control. Be honest and true to your team if you do not know certain fields in technology.

Apart from being honest with your team, you must also be transparent and true to your words. Avoid situations where you say something to your team but mean something else or would do something else. Once you have made a commitment to your team, you must stick to your word.

Pizza, beer, and a night out will also not be sustainable. Treating your team to food and drinks will only get you so far. Pizza has a reputation for overtime kidding aside. You can't buy respect; doing this early on may even raise suspicion that you are compensating for your leadership with alcohol. There is nothing wrong with a Pizza and Beer night out, but I suggest doing this once you have already established your identity and the trust of your team.

Reminder: Let me borrow a quote from the Book "Why Should Anyone Be Led By You". To gain the respect of your Technical Team, you should become a "authentic chameleon" meaning as a leader you must adjust to circumstances yet remain true to who you are and stay consistent to your team.

Lesson 8: Show Your Human Side

Nobody will follow or respect a cyborg, mutant, or a corporate superman leader. To build a winning team, a leader must show his real non-fatal weaknesses or flaws to his technical team. This makes his team see him as human, and they would be willing to complement the shortcomings. By showing your weaknesses, your team will likely remain or stay together with you because they would know they can be of help to you. Therefore, a leader must reveal his non-fatal leadership flaws. Let us show some examples of fatal and non-fatal leadership flaws.

Fatal Leadership Flaws to Avoid

1. Indecisiveness

2. Fickle

3. Frivolous

4. Cowardly

5. Irresolute

Non-Fatal Flaws of Leader that Enhances His Leadership

1. Fear of heights

2. Fear of spouse(In my case my wife)

3. Unable to sing

4. Unable to dance

5. Outdated fashion

6. Introverted attitude

7. Mild Cockiness

8. Outdated on some technology trends e.g. Tiktok

Real-life Non-Fatal Weakness by Example:

"A leader is trying to study infrastructure as code because he knows nothing about it and wants to occasionally participate in the code review process. This is a non-fatal flaw because it shows that you know nothing in some areas that your team does but are willing to learn so you can add value to them."

"Looking deeply troubled in front of your team mates only to find out by them that you were worried how to solve your daughter calculus homework."

Reminder: Reveal and show your non-fatal flaws at the same time fix your fatal flaws otherwise expect your team to leave you.

Lesson 9: Help Them Craft Their Career Path

The greatest accomplishment of a leader is to see his prodigy become better than him. Borrowing John Maxwell's terminology, this is called Level Five Leadership. The most inspiring thing you can do for your teammates is to show that you genuinely care for them. There is no better way of showing genuine care than through unsolicited coaching and mentoring. In my case, I always conduct a formal one-on-one coaching session with each of my team members once a month, and then I share knowledge with them informally on a weekly basis.

Knowledge sharing can encompass anything: whether it be technical, leadership, management, real-life experiences, past mistakes and regrets, or practical skills. Asking individuals where they want to be in their careers also helps. As a leader, it is your job to guide and influence their lives based on their future goals. A leader who generously shares valuable knowledge earns respect from their team. Do not be the leader who adds no value to their team; give your team an energy.

How do you know you add value to your people? When you feel fulfilled on each and every mentorship session with your team, and when your team feel refreshed for each wisdom you share.

Reminder: Be a giver not takers. Borrowing a quote from the book "Give and Take". The least successful people at the start of career are the givers while mediocre people are the takers from start to finish, surprisingly those that remain givers at the later part of their career are the ones who really succeed belonging to the top 10%.

Conclusion:

Even though you created the best of the best called GOAT Team. Be mindful that your team will not be forever. Therefore, you must ensure to be happy for them when the time that you as a leader will be outgrown by your prodigy or when the time comes that they are about to leave. Always put ego at the backseat. Be the person you wanted to be when you were once junior.

References:

Leaders Eat Last - Simon Sinek

Why Should Anyone Be Led By You - Robert Goffee and Gareth Jones

Starts With Why - Simon Sinek