Finding the winning difference with milestones

Sara Holmberg
February 9, 2024
Finding the winning difference with milestones

Milestones are a big deal! Just think of those big birthdays, graduating, getting married, buying a house, becoming a parent…they are all momentous occasions in our lives and times, we rightly, remember and reflect one.

Now they might not be as big, but we have milestones in our professional lives too. We want to invest our time and energy into becoming better versions of ourselves, we might want to learn a new skill, we might want to get that promotion at work…the list goes on.  

And (while we’re full of the best intentions) often we end up swiftly waving goodbye to our grand aspirations as they disappear in the rear-view mirror while we hurtle from one thing to the next. Once this happens, it’s oh so easy to fall into the trap of beating ourselves up because we feel like we haven’t achieved everything (!) we set out to do. We focus on what we haven’t done rather than celebrating what we have done - without pausing to consider if it was realistic or achievable to start with.

Teams are certainly the same. At Winningtemp we talk about Milestones (that are also a feature in our product) as a more structured conversation between a manager and an employee. Many other companies call these structured 1:1 meetings performance reviews or appraisals 😉  

We believe it’s important to stop for a moment and reflect. Because teams can both feel like they’re failing when they’re not hitting goals or reaching milestones - and no one wins when this happens. So why don’t we flip this around and help teams (and everyone in those teams) perform to the best of their potential… and feel good about it?

Here are several reasons why milestones and structured conversations are important:  

1. Set goals and measuring progress

Milestones allow individuals and teams to assess how far they have come and how much is left to achieve. Milestones also make it easy to set goals.

And setting goals brings clarity that is transformed into collective understanding for what a team need to do to reach their objectives. Like this, each team is aligned to their individual, team, and organisational goals.... resulting in a sense of unity and shared purpose.  

2. Increase communication and collaboration  

Milestones ease transparent communication within teams and organisations. Because you have a common understanding of progress, you ensure that everyone is on the same page, and are doing their part. This means that every team members know what to expect from each other and their collaboration, which helps to achieve specific objectives, and creating a fun, collaborative and cohesive work environment.

3. Dealing with unexpected challenges

When obstacles are encountered, milestones provide a framework for adapting plans. Teams can reassess and modify strategies to overcome challenges and continue progressing - which is much easier when everyone understands the milestone they’re working towards.

4. Celebration wins

Milestones offer moments for acknowledging and celebrating achievements. Recognising the completion of significant tasks or goals boosts morale, promotes a positive culture, and reinforces a sense of accomplishment. Celebrating milestones creates a positive feedback loop, encouraging individuals and teams to continue striving for excellence.  

5. Set performance development plans

Milestones serve as natural points for evaluating performance development. Regular assessments allow for reflection on what worked well, what could be improved, and how to enhance future efforts. By analysing performance development at each milestone, individuals and teams can implement continuous improvement strategies, optimising processes and outcomes.

Milestones are essential tools for progress tracking, motivation, goal alignment, and effective communication. They contribute to the overall success of individuals, teams, and organisations by providing a structured and manageable approach to achieving objectives.

Best practise for holding milestone meetings

In general, the meetings include talking about employee's personal development, work situation, and cooperation within the team, among other things. It’s a time for reflection, constructive feedback, and talking about the employee's job satisfaction and ambitions.  

In many companies, these structured conversations are held on an annual basis and tend to be very time consuming for both managers and employees.  

Research has shown, however, that it’s more motivating and engaging to have shorter but more regular conversations and check-ins between manager and employee. The relationship becomes stronger; it's easier to identify strengths within the individual and the team, as well as possible risks for stress or burnout.

At Winningtemp we want every employee to feel they have the possibility to develop and grow. We expect everyone to have regular 1:1 conversation with their manager regarding personal development, wellbeing and follow up on objectives. We can have different preferences regarding the frequency of formal milestone meetings, but we encourage everyone to have at least one dedicated structured face-to-face milestone conversation each quarter between manager and employee.

Want to find out more and take a step closer to finding your very own winning difference? We’d love to help you figure out the best way to make milestones work for your business.

Let’s talk!

With a strong background in legal and HR consulting in firms such as Fingerprint Cards, PwC and Flex, she joined Winningtemp as Head of HR in August 2021. Sara is passionate about people and believes that the future of work and HR is moving towards an approach where employees feel valued and have the tools to reach their potential. To achieve this aim, she’s focused on working to give employees their desired level of autonomy within their roles, creating a rewards system that focuses on recognising and understanding the needs of employees, from financial welfare to mental health. Additionally, her commitment to wellbeing is shown by her work as a board member at Räddningsmissionen, a Swedish charity working for social rights ensuring everyone has access to a dignified life.

About the author
Sara Holmberg

Focusing on people

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