Fail fast is a frequent maxim in business, but what about reverse engineering that concept? We sought technology leaders who could advise on succeeding fast, along with creating a strong organization, developing team leaders, leveraging the support of peers, and specifically how to streamline day-to-day management of a technology group.
Here is the main the question we posed: If you were writing your own book on how to lead, what advice would you impart to other technology executives?
Influential CIOs and other technology leaders responded with time-tested, hard-won knowledge and guidance. And their tips ranged from sweeping advice on building an organization to specific tips for managing time.
Check out these strategies for leading well based on decades or experience from the C-suite.
Lean on your peers
Tech leaders should seek out areas of common benefit with executives and other peers, says John Cannava, CIO at Ping Identity. In these interactions, he also looks to avoid the projects colleagues aren’t enthusiastic about.
“Perspective about where current or future initiatives will have support is invaluable,” Cannava says. “Look for insight on what will be easier to prioritize, fund, resource, and get meaningful executive sponsorship.”
Cannava says developing authentic personal relationships with your peers can help key in on areas of natural alignment — and avoid wasting time on projects where it’s unclear how to measure the outcome.
“If leaders prioritize and exemplify transparency and partnership, they’re setting themselves, their business, and their employees up for success,” he says.
Build a strong foundation
In part because he was raised in a military family, Adaptavist CIO Neal Riley finds inspiration from historic leaders, such as this quote from Winston Churchill: “We design our surroundings, and then they influence us.”
Riley describes a company’s surroundings as the tools, platforms, and applications used to get the job done.
“The most important thing a tech leader can do is create the architecture that staff work with,” Riley says. “After that, the architecture begins to shape not only your employees but also yourself and the entire organization.”
Josh Langley, CIO at Iron Mountain, says he tries to display the characteristics he believes are important to creating a strong foundation for an organization: authenticity, transparency, trust, and accountability.
Langley sets up bull sessions each quarter with his entire organization for feedback he says has improved his leadership.
“We have candid discussions about anything from our enterprise strategy to how we manage work-life balance,” he says. “These frank conversations have led to improvements in the way I lead the team as well as how I find balance in a very busy work environment.”
Turn employees into leaders
The best leadership hack is a self-sustaining one, says Chetna Mahajan, chief digital and information officer at Amplitude: Create an environment that produces more good leaders.
“It’s important to empower employees, especially your leaders,” Mahajan says. “This means understanding their strengths as well as their weaknesses. I strongly believe in situational leadership. You need to know what development level the leader is at, and then you can create your strategy for managing them and supporting their growth.”
Andrey Ivashin, CIO at Dyninno Group, says a key part of building a great team is identifying the members who are ready for the next step.
“It’s your duty to support and inspire someone who is already extremely driven to improve,” Ivashin says. “You should first consider your people and provide them with prospects for professional advancement. This is a quality that every manager must possess. One day, your employee should say, ‘Yes, my manager helped my career progress.’”
And, on the flip side, it’s just as important to be mindful of team chemistry and take action when there’s a problem, says Srini Kadiyala, CTO of OvalEdge. Bad hires happen, and sometimes, promotions don’t work out.
“Don’t be afraid to swiftly move individuals that do not make the team perform better out of the team,” he says.
Be human-focused
Theresa Payton, former White House CIO and now CEO of Fortalice Solutions, says her best tip for tech leaders is to focus on human-centric design, which leads to lasting relationships with customers.
“Whether navigating emerging technologies or leading digital transformations, placing human needs at the forefront enables CIOs to drive meaningful innovation and create solutions that truly resonate,” Payton says.
And keep in mind that creating a healthy work culture will be reflected in the products you deliver.
“By fostering a culture of empathy, curiosity, and collaboration within their teams, CIOs empower their organizations to deliver impactful solutions that drive value,” she says.
Precious Abacan, CTO of Softlist.io, says the best advice she’s received about leadership in technology was simple and direct: “Give people breaks.”
“My mentor once told me, if a team member is struggling — whether they’re stressed or dealing with personal issues — encourage them to take a few hours off, enjoy an extended lunch break, or even a full day off if possible. It’s important as a leader to prioritize a culture where health and well-being come before work.”
These gestures are meaningful and leave a lasting impression, she says, noting that she remembers every instance where she was offered such help. “Now, in my leadership role, I make sure to extend the same kindness.”
Make meetings matter
Meetings should be consistent and brief — and foster understanding and consensus, advises Mike Fitzgerald, partner in Infosys Consulting’s CIO Advisory practice. And he says one of the most important things you can do to make meetings better is to right size the attendants list.
“Having too many people participate constricts honest discussion and can be very expensive,” Fitzgerald says.
A well-organized meeting can help reduce isolation in technology teams, argues Megan Alarid, whose consultancy The Heightened Leaders advises executives.
“Communicating is the biggest challenge in business — any business — so over-communicate. Daily scrums, stand-up meetings, weekly tactical team meetings that have nothing to do with the work but everything to do with the team. It’s imperative to keep the team in the know, so that projects can stay on track and under budget,” Alarid says.
Langley offers a few rules that he shares with his teams, which can reduce avoidable meetings and ones that lack intent, while keeping meetings efficient and productive.
Every meeting must have an agenda, and he calls setting time for actual productive work during the meeting “sacred.” He ensures decisions are made at the end to avoid follow-up meetings, and he keeps meetings short.
“Fifteen minutes is the default, thirty is allowed. An hour is the max,” he says. “And don’t fall victim to FOMO. Skip meetings that don’t need you, have too many attendees, or lack focus or intent.”
Narrow your focus
Todd Wynne, CIO at Rogers-O’Brien Construction, says early in his career a manager pulled him into his office and offered some of the best leadership advice he’s ever received, which allowed him to home in on what’s important to deliver results.
“He pulled me into his office one day and told me: ‘You’ve got a lot of good ideas here, but the enemy of a great idea is five good ideas. If you spread yourself too thin, you’ll never make the kind of impact you want. You need to focus on your most important thing — your M.I.T.”
The meeting took him aback, but it was a turning point in his career, providing new clarity and purpose.
“I went through my list of ideas, scrutinizing each one. It was a humbling experience but also enlightening,” Wynne says. “By narrowing my focus, I found I could dig deeper into problems, finding solutions that were more than just surface-level fixes. I’ve carried that lesson with me ever since, using it as a guiding principle. So whenever I find myself pulled in many directions, I pause and ask, “What is my M.I.T.?” And just like that, the fog clears, and I know exactly what I need to do.”
Accept inconvenient challenges
Marcelo Lebre, president and CTO of Remote, says sometimes the best opportunities appear at surprising times.
“Back in 2012, my girlfriend dragged me to have coffee with a friend and her boyfriend,” says Lebre. “I didn’t feel like going, had just moved to a new city the day before, and was starting a new job. But I ended up going anyway.”
On that coffee break, he ended up meeting his future startup partner, now the CEO of his company. “Seize opportunities,” Lebre says, “even when they seem inconvenient.”
Langley advises future leaders to stay open to the next step, even if the path forward is uncertain.
“I tell people to just say yes. When asked if they’ll take on a new role, new responsibilities, a new project — just do it,” he says. “It may be challenging, and it may not be in your area of specialization, but that’s okay. You learn so much by stretching yourself, and you are likely being looked at as a trusted leader.”
Krithika Bhat, CIO at Pure Storage, advises embracing daunting challenges, even if you feel unprepared, because those opportunities in particular lead to personal and professional growth.
“Rather than striving to meet every requirement of a role, embracing roles outside your comfort zone expands your skill set and introduces you to potential mentors and allies who can support your journey.”
David Habib, principal at consulting firm Wren’s Watch, says when deciding to take a risk, it’s important to be clear what success means to you.
“I’ve mentored dozens of IT leaders over the years,” Habib says, “and in every case I’ve stressed this: If you know what you want, you’ll be prepared to grab opportunities that will advance you toward that goal. If you wait for your career to happen to you — well, you’ll get what you get.”
IT Leadership, IT Strategy, Staff Management
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Source: News