Managing and assessing the team

As a manager, you must assess performance and provide critical feedback to individuals in the team. This feedback should not only highlight what the individuals do well, but also their areas for improvement. If there are problems, ensure that you have the hard discussions fast and quickly, and not let issues pile up or ignore talking about problems.

Regular 1:1s

Recurring 1:1s are a great way to establish connection between employee and manager and to share the common goals and set deliverables to measure progress and outcome. It's advisable to split 1:1s into two separate categories, that is, ones that focuses on tactical day-to-day statuses and tasks, and some, less frequent ones that are there to discuss long-term career growth. The more frequently ones should probably occur once a week, but it depends on each individual. Some people need more management advice and guidance compared to others.

A critical part for the individual pen tester is to get together and set career goals. For some, pen testing is an intermediary stage that they might want to perform for a few years, but career goals are related to other goals. It's important to understand the long-term goals of everyone on the team so that the right projects, challenges, training, and opportunities can be made available to support learning and career growth.

Conveying bad news

Conveying bad news is tough, and typically individuals know when they've made a mistake. In my opinion, there is little value in repeating the root cause and continuing putting salt into the wound when someone is already fully aware of their mistake.

Rarely, someone might not realize their own deficiencies or problematic behavior and, if this is the case or someone else provided negative feedback, it is your responsibility and duty to convey such messages. Since this is the opportunity to learn and improve, the key aspect is to highlight criticism or call out negative feedback in a private setting and not during a team sync or standup meeting. This includes tough conversations, such as the creation of performance improvement plans, if they do not perform well or negatively impact others on the team.

One thing that I stated earlier, and that I want to repeat here, is that, if the team fails, it is the leader's fault. No one else is to blame. Step up and take responsibility if you are the leader.

Celebrating success and having fun

When it comes to the good news, it should be widely celebrated and praised. Everyone works hard and recognizing success is one of the simplest yet most effective ways to acknowledge the critical role someone performs within the organization.