Essential Soft Skills for IT leaders in a Remote World

Contrary to the myth of the solitary tech visionary, industry veterans know that IT has always required collaboration and teamwork. But recent trends suggest that so-called ‘soft skills’ will become more fundamental to IT projects and organizations. Take cybersecurity: 82 percent of CISOs interviewed in a recent Kudelski Security study consider skills like communication to be critical for hiring, compared to 52 percent for hands-on technology experience. So while technical and process skills remain foundational, the next generation of leaders from all IT branches will make their mark with people skills. 

Soft skills have been gaining value among CIOs and hiring managers for years, but demand for non-technical abilities has reached a tipping point. CompTIA found that 62 percent of respondents to its “Workforce and Learning Trends 2020” report ranked soft skills on par with technical skills in the hiring process. The reasons for this shift? On the innovation front, technology has become critical to nearly every function of an organization, increasingly facilitated by third-party cloud applications, meaning the days of siloed IT teams are quickly coming to a close. Second, the tech talent gap: many organizations struggle to fill IT positions, given heightened demand for technology skills. To recruit top candidates, companies need to show their commitment to providing a welcoming and empowering work environment. 

Next, consider the impact of the pandemic. Government restrictions pushed teams into remote working arrangements overnight; to adjust to this digital-first climate, companies adopted new technologies in droves. In short, IT organizations are becoming more dispersed just as demand for cross-functional tech leadership is growing. In this dynamic environment, the ability to communicate and collaborate cannot be taken for granted. The time for “soft upskilling” is now. 

However, cultivating interpersonal skills is not as straightforward as learning a new programming language. The list of applicable soft skills is nearly limitless, and there is no single credential that certifies abilities that many consider innate. Fortunately, soft skills are almost always transferable and complimentary, so there is no wrong way to learn. To start, here are three essential soft skills that every IT leader should develop: 

Earn trust through vulnerability

Effective leadership always requires establishing mutual trust and respect. But this can be a challenge for today’s teams, which are more geographically remote—missing out on non-verbal and body language cues that make up 93 percent of communication—and cross-functional, meaning members may not share a common expertise or specialist language. To connect the dots, IT leaders need to follow a somewhat counterintuitive logic: be authentic and vulnerable. 

People in positions of authority often aim to project unbreakable confidence, but a better path to building connections is through honesty. Foremost, being open about insecurities, uncertainties, and failures is humanizing—a critical trait in the age of Zoom. Conversely, ultra-strict managers may find their teammates become reticent to speak up about risks they see. Such an environment is an anathema to multidisciplinary IT fields, given the need for transparent workflows. 

Being vulnerable at work is not only about you trying to show something to your teammates, it is also about establishing and growing a safe environment for the colleagues you work with. In my experience, it’s hard for people to speak up about sensitive topics like challenges, difficult conversations or if they don’t agree with someone at work. But these aspects are much easier when the team, including leadership, has built an environment, where everyone trusts that they are free to express their opinions and share their feelings about their work

How do you build this safe environment if you can’t even see your colleagues face to face? 

First step for a leader would be to start with honesty and a commitment to be your authentic self. In order to achieve this, you need to learn what you can share about yourself and where you would set the boundary between personal and professional life. Before showing vulnerability and sharing some personal information, you need to define what kind of information you can share. To define boundaries, you need to define for yourself, for the environment you work in, for the team you work with, what is acceptable. 

For example, you can share a few bites of information about your family. At the same time before starting a meeting, instead of just silently waiting for everyone to join, you can chat with your colleagues about casual things like vacation plans or ask how their family is doing. Keep in mind that you have to be careful when sharing information with anyone at work. Do not overshare something too personal. 

For example, if you mentioned that you were in a relationship and this ended recently, do not share extra information about who initiated the breakup and how it went, etc. Before sharing such topics, try to imagine how you would feel if a colleague of yours would share something similar with you. How would you feel about that? If the answer is - I would support, understand or suggest going for a drink, then it’s a good bit of information and you can share it with your colleagues. One more important thing to remember - do not gossip about anyone, you can share only your own personal information, not others.

Build a collaborative environment 

Research shows that workplaces that promote transparency and authenticity benefit from improved employee engagement and confidence. What are the building blocks of open communication? First, team members must feel that they are in it together, that they are building their product together as a team, and that everyone can share their honest opinion. Frequent, sustained and meaningful interactions between members—encompassing project-related collaboration and shared “rituals” like regular meetings, “cake and coffee” and other social gatherings—have been shown to curb our natural tendency to build relationships with select team members, and rather invest in more team connections. The more we learn about people we work with - the more we trust each other. Team members, who know and understand each other are more productive and more accountable in what they are working on. 

But is this possible in virtual settings? In fact, tried-and-true team-building exercises can be adapted to remote settings, with an added boost to innovation made possible by the greater diversity inherent in dispersed teams. But leaders must prioritize these activities amid competing demands while also creating tech-enabled processes and protocols that mimic face-to-face communication. Exercises that tie individual motivations to an organization’s mission are a practical entry point.

There are a few more team activities, which can help to build a collaborative and safe environment:

1. If something failed in production or a bug was found, try to establish “Five Whys” practice as a new normal way to identify the root cause of the problem.
2. Leverage User story mapping technique and miro boards for collaborative planning of the future tasks for the team.
3. Give kudos to each other for a great job and celebrate team achievements together.

How to find a root cause of an issue

One of the tools I used to identify the root cause of a problem is “Five Whys”. A problem could be a technical issue, like a bug or failure of the system, or non-technical, for example, something went in an unexpected way, not all tasks were done, etc.

Method of Five Whys is very effective but be aware that in the process you can potentially discover something unusual, something that you never thought of, something about your system which can improve it drastically. Let’s imagine that something went wrong on production (software or hardware issue) after you released a new feature, and you want to investigate what actually went wrong. Normally you would probably blame some code which was broken and feature implementation, which broke production. But that is not always true. 

For example, when you have an accident, it is better to define what we are investigating. Let’s say this incident is about something that wasn't working on the website. In this case you should bring all the people responsible for this deployment, feature development and feature discovery to sit together at one table. When everyone comes to the meeting, you need to ask “Why?” five times. First time could be confusing and not clear. Second time it would be even more confusing, but then on the fifth time you ask “Why did this happen?”, you will get to the root cause. You could discover, for example, that it is not that the feature was not developed correctly or somebody made a mistake in calculations. It could be that some of the parts of the feature were not tested enough or were not covered by the tests. That means that your testing strategy could be improved. So when you run this “Five Whys” meeting, be prepared to discover something unusual, something that you didn’t see before.

I personally ran a “Five Whys” meeting as a postmortem for an incident after an unsuccessful release. Any team can fail to release a new feature, it’s quite usual in the IT world. But when you bring the team to discuss the issue, everyone would expect to be blamed for not performing well enough, for not doing a great job. As a leader, your goal is to make sure that everyone in the team is fine with accepting a failure - that is how we learn what to improve to build great products. When I invited everyone to join a meeting to investigate an incident, everybody was very nervous and tried to prove that they did not do anything wrong. 

Instead of looking for someone to blame for a mistake, we wrote a step-by-step description of how we performed this release. And then I asked “Why did it fail?” five times. At the first and even the second iteration we could not figure out the real cause of this failure. On the fifth step we realised that the real problem was that our testing environment was configured differently from production. This discovery was so unexpected that the team members got super excited to fix it immediately and improve our release process. Also the mood in the meeting room changed - at the beginning everyone was troubled and insecure, at the end of the meeting everyone was keen to improve and happy to discover such an improvement to be made.

Make candid feedback a habit

It is not enough for the CIO or CISO to reveal their own flaws. They must create an environment that facilitates two-way communication on challenges and mistakes without defensiveness or fear of reprimand. 

This spirit applies equally to ad hoc reviews and formal evaluations. For example, a cornerstone of the Scrum product development strategy is the Sprint Retrospective, wherein the team reviews recent collaborative work in-depth and identifies improvements to implement. To avoid these kinds of exercises devolving into finger-pointing and tears, facilitators should steer the conversation with “powerful questions,” or open-ended queries that cut across day-to-day issues to illuminate deeper obstacles preventing progress toward goals. 

Supporting team members in their personal growth and development is very important while working in remote and distributed teams. How can your teammates know if they are doing the right steps on their learning path and in their jobs? As a leader of a team, you can always provide honest feedback, which should motivate and help the person receiving it.  Kim Scott calls such feedback “radical candor”. Her technique of giving feedback would help to encourage and point out areas, which need to be improved to do a better job and to get more experience from daily tasks. The key is to show that you care and not to hurt anyone’s feelings, but guide them to success.

If you would like to improve not only your feedback skills, but make your feedback more effective for each member of your team, you need to learn more about your colleagues’ core values. There are a lot of benefits to knowing the core values of your team members:

• You will understand what is more important for them
• You will learn how they take their decisions, as everyone lives up to their own standards
• Knowing your team members’ values would give you more clues as to what is more important for them. This could improve how you help them to build their career in the organization and how to build a safe environment for them

To learn something about yourself and your colleagues there is an easy way to run the workshop. It could take up to one hour or maybe a bit more for thinking and talking to each other depending on the team size. But this exercise will help you to learn more about your colleagues and appreciate each other for your strong values, for the personalities, for how the team behaves at work and what you all care about. This workshop is called “Define your values”. As you can see, the list of values is huge, but you should consider which are most defining your personality and your behaviour. This means thinking about which values you keep integral to your work days, at home, in your personal life. Just look at this list and pick two of them. You can do the same with your colleagues, with your team or somebody with whom you work, or run this as a workshop in a team event. This can help you to learn more about your colleagues and what they care about. Whenever they take a decision, they will follow these values, because these are their principles in life.

Upskilling for the next normal

As qualities for a successful leader—communication, collaboration, problem-solving, the ability to inspire and motivate—soft skills are nothing new. But these traits are taking on a renewed importance in our disrupted and transforming world. If nothing else, COVID-19 and other recent global events remind us of the importance of humility, transparency, and trust for thriving amid the unexpected. 

Nowhere is this more true than in IT, which is experiencing renewed appreciation and expanded responsibilities in the rush toward digitization. More than ever before, IT leaders are in a position to shape the future of their organizations and create societal benefit. We would be wise to toss out the outdated model of the tough boss and realize the possibilities of leading with vulnerability, empathy, and care. 

About the Author

Anastasiia Tymoshchuk has more than 10 years in software development, including experience in e-commerce as well as game development. Every day she deals with lots of challenges starting from designing a suitable architecture, as well as building best practices in the team. Currently she works as a Tech Lead at scoutbee, serving her team's needs as a Servant Leader. Anastasiia is also one of the organisers of PyBerlin meetup based in Berlin.