The complicated parts of leadership: Betting on people

In this series of short stories, I share tricky situations I’ve encountered while leading teams. These experiences have taught me invaluable leadership lessons and greatly influenced my management style. I hope to help others become more effective leaders by sharing these anecdotes.


Do not invest in that team, do not renew their contract; let it expire; it’s not worth the effort”

The outgoing manager of team I was going to lead


Another day, another reorg – things were constantly changing in that company group. After the dust settled on the latest reorg episode, I would own a critical charter: everyone needed it, but nobody wanted to touch it with a ten-foot pole. 

My technical expertise and past experience made me a natural fit; however, it was the perfect maelstrom of chaos: from unhappy customers to burnt-out engineers, from broken products to suboptimal engineering practices

As part of that change, my team expanded to include a group of contractors in a different timezone. During handoff, the advice was to let them go. The previous leader strongly discouraged continuing their contract, citing their lack of productivity. Although he encouraged me to form my opinions, his overall outlook on the situation was bleak. 

Understanding the background

The obviousness of the contractors’ struggles was offset by the obscurity of the underlying reasons. Were they appropriately onboarded to address the complex product demands, or were they simply disinterested? 

I started gathering information, and as I delved deeper, I realized that the original team had done little to fully train the contractors. A few interviewees agreed that the lacklustre performance was commensurate with the training provided, and some admitted that the contractors were not set up for success.

Deciding to invest or cut losses

The safer option was to follow the oft-repeated advice and not renew the contract: the team had too many fires, and it was necessary to focus on a few things and avoid getting spread too thin.

A riskier alternative was to invest in development. However, if my bet on skills acquisition failed, the team would lose all the hours spent on training and development, and the fallout would include the classic “I told you so”. If the bet succeeded, the team would benefit from orders-of-magnitude productivity boosts. They were in a different timezone, and their handling of off-hour calls would bring respite from the constant nightly outages. That, in turn, would help us accelerate our investments into permanent fixes.

I decided to bet on the team and give them a chance. I was prepared to take full responsibility and ownership for whatever outcomes emerged.

Don’t miss the next post!

Subscribe to get regular posts on leadership methodologies for high-impact outcomes.

Join 272 other followers

Following through

This meant focusing on writing documentation, recording introductory videos, and setting up knowledge-sharing sessions. I also crafted a training syllabus to measure progress and track accountability.

At first, it was a struggle – they kept falling back into their old habits and not following the training regimen. But after finetuning and feedback sessions, we finally found a routine that worked for everyone, and things started to come together.

The first signal of improved productivity was the uptick in independently-resolved issues – they started addressing complaints without asking for help. Then, it bloomed, and within 3 months, they were on par with just about any engineer on the team.


Their productivity quadrupled within that period, and the extra help gave the team the much-needed breathing space to exhale. Furthermore, they started contributing to the documentation and training of new hires, scaling our wins. The turnaround was so remarkable that even the naysayers acknowledged the reversal – one sceptic confessed that he had already written the team off.


Against all odds, the maligned team successfully transformed into critical contributors. All it took was giving them a chance and investing in training.

This experience left me wondering how many teams could be transformed with the proper investment in training and development. And also how many teams are struggling because they are too busy to invest in training.

Sometimes, doing the counterintuitive thing is OK if it means granting folks opportunities to excel. Bet on people – it costs you nothing, and the upsides are marvellous! 

Tips for betting on folks

  1. Have skin in the game: It takes courage to embrace the possibility of failure. You must push past your discomfort and genuinely believe in the team’s abilities. 
  2. Stay curious: Maintain your curiosity, even when confronted with obstacles. Consider various factors and tackle the situation with a confident and kind demeanour. Assume the best in others to foster strong and constructive relationships.
  3. Verify: Have accountability checkpoints, and don’t let things run in auto-pilot mode.

Next story: trust and verify

Don’t miss the next post!

Subscribe to get regular posts on leadership methodologies for high-impact outcomes.

Join 272 other followers

4 thoughts on “The complicated parts of leadership: Betting on people

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.