Having honest career conversations – an event with GroHappy


Having honest, open career conversations is something that a lot of us – individuals and companies – find a challenge. Following the success of our last event, we learned that the topic that people most wanted to explore further was ‘how to enable honest career conversations’.

We brought together thought leaders, talent leaders and talent professionals for an informal breakfast event to share experiences, challenges and ideas on how to enable better career conversations. In reality the discussion became much broader and touched on career pathways, career progression as well as career conversations.

The morning began with networking over breakfast at Grant Tree’s workspace in Clerkenwell, who hosted us on their stunning rooftop terrace.

After breakfast, the event kicked off with an introduction by GroHappy founders Jim and Karinaabout some of their own experiences with career conversations. In particular, Karina noted that they were seeing more and more organisations focusing on the power of conversations to engage and retain employees.

Guest speakers were invited to share their perspective on the value of honest career conversations and what they are doing to enable better conversations in their workplace.

Introducing the speakers

Richard Goold, Lead Partner for People & Talent, Moorhouse

Richard Goold from Moorhouse spoke first, drawing parallels between the recent Royal Wedding speech by Reverend Michael Curry and career conversations. While Reverend Curry spoke of the power of love, Richard imagined a world of business where love was the way. Where people could support each other and that everyone could progress and flourish, without the need for ‘sharp elbows’. Honest career conversations were key to this as well as recognising the reality that people will at some point choose to move on.

He highlighted the importance of trust in enabling companies to move at high speed. In high trust environments there’s no need to ask qualifying questions or to second guess people. If you can trust what is being said in a career conversation, then you can make the right moves, quickly.

“Trust is gained in inches and lost in feet.”

Richard also explored how the world of work is changing. People have many different career paths and they need to be equipped with a compass and not a map. Instead of climbing the traditional career ladder in the same company for 15 years, with a clearly defined map of where you’re going, people now spend two or so years in one place and then move to another. Organisations, therefore, need to help people shape their own identities and navigate their own career paths.

Richard spoke of a negative leaver experience that he had when leaving a previous employer and somewhere he had worked for several years. He talked about how this diluted the goodwill that had been built over many years in a very short period of time and the significance of nurturing relationships so that we are continually building goodwill with our people.

“Silicon Valley has it right, they make their leaving process as exciting as their joining process.”​

By doing so, it increases the likelihood of people returning in the future.

Finally, Richard advised on how conversations need to move from “getting through” meetings, to “getting from” meetings. We need to move from punctuated monologue (for example, through emails) to an active dialogue where the person you’re talking to is the focus point and where there is space for unstructured conversation to flow.

Attendees each received a postcard with 3 insightful questions that Richard uses to open up a career conversation:

Debbie Martin, Chief of Talent Experience, AND Digital

Debbie Martin from AND Digital added to this in her talk, when she said, “Career paths are now so much more bespoke and varied.” Because of this, honest career conversations are more important than ever. She illustrated the rise of portfolio careers and the gig economy with some of her own experiences. Debbie highlighted that today’s workforce might have around 10 different jobs and three different careers throughout their lifetime.

Because of this, many employees aren’t looking for a linear, clear-cut career path. Instead, they want to build their skills. People want as many transferable skills as possible.

At AND Digital, some employees have returned to work after taking a alternative career route, such as two years as a personal trainer. Another has left to start their own ice cream company, and a candidate recently mentioned a side venture in natural beauty products.

Side projects are built into AND Digital’s culture and DNA. You’ll notice that many people from AND Digital have both their business role and their side hustle/project in their LinkedIn job title. This is part of enabling people to bring their full selves to work and recognise that, some people, have creative passions in addition to their role at work.

Honestly addressing this in career conversations is critical. Debbie also advised that those conversations need to be an ongoing dialogue, instead of limited to annual or biannual conversations around the review.

Finally, she explained that there was a difference between being a line manager and a career coach – and that managers needed to understand this and to be ready to wear ‘different hats’ at different times. Giving feedback on a deliverable is a line manager’s duty. Supporting someone’s longer term aspirations and how current projects feed into this is the role of a career coach.

Sophie Theen, Head of HR & Talent, 11:FS

Sophie Theen at 11:FS capped off the talks with her own experiences in a large global technology firm as well as her current role as Head of Talent at a startup. In the global company she explained that she was given a map to follow, with a distinct career path. Eventually that led her to a managerial position where she found herself doing less of the work that she was passionate about and more time managing processes and ticking boxes.

Therefore, she decided to move to a startup environment where she had more autonomy and could move quickly with new ideas and initiatives. Sophie shared how she deliberately thinks about how not to operate like a corporate. However, the start-up environment posed some new challenges.

Notably, in a startup there’s often more rapid progression. Someone in their twenties could quickly find themselves in a manager role or even VP role. Sophie discussed the importance of support people, who might be first time managers, with the tools and training that they needed to become effective leaders.

Sophie shared how not every manager knows how to have honest career conversations. The challenge, therefore, is to find the right mix of technology and training to allow those managers to have the right discussions with their teams. In 11:FS, they have found that tools can facilitate this and ensure that conversations do happen, even when the business is running at 1000 miles an hour and everyone is really busy.

Questions for the speakers

The introductory speeches were followed by a Q&A session where each speaker was asked questions about equipping managers to have career conversations, building a culture of trust and how to keep conversations going when a company scales.

Richard highlighted that sometimes managers and leaders do mess up and get things wrong. Companies need to train managers to understand that it’s okay to admit when they’ve made a mistake. That helps to build a culture of trust. It also encourages managers to keep learning, as when managers stop learning, the organisation stops learning.

Debbie seconded this by saying that managers need to understand humility and when they cannot help an individual. When someone has a drastically different career path, managers need to seek additional help through mentors or their extended network.

Sophie addressed the scaling question, by reinforcing the need to be honest. Especially within a fintech start-up like 11:FS, people aren’t going to be there for life. They’re there for the experience. Companies need to get the fundamentals for each individual right from the start. What are you trying to achieve? Where do you see yourself going?

Richard highlighted the accountability of each person who manages a career conversation.

“Be strict about who you pass the torch to,” he said, “it is a privilege to look after people’s careers and you can destroy someone’s career if you hand the torch over to the wrong person.”

“Be strict about who you pass the torch to. It is a privilege to look after people’s careers and you can destroy someone’s career if you hand the torch over to the wrong person.”​ – Richard Goold

Patterns from the group session

A group workshop followed where attendees were able to create some actionable steps to take back to their own organisations. Jim, Karina and Eoin guided each of the groups through an activity designed to explore current challenges and solution ideas.

Here were some of the key themes that emerged:

  • Leadership enablement – strong role models who can show vulnerability and honesty about how they’ve been helped in their careers. There was a focus on specific training and enablement for leaders including EQ, unconscious bias and coaching skills, as well as these skills becoming key in leadership selection.
  • Providing the right training and tools – when a company is growing and changing quickly, it is a challenge to ensure that managers and employees are equipped with the right tools – including those to enable effective career conversations. One way that many organisations are addressing this is having a dedicated onboarding process for new managers to give them timely, accessible support.
  • Career ownership – employees taking the driving seat for their career development and growth was a key theme. While HR and managers play an important role, employees need to own the career that they want to build. Often this is a mindset shift that individuals need or value support on.
  • Pathway vs compass – there was a recognition that some employees crave a structured path to follow, while others crave flexibility and freedom. How might companies balance the two? There was good discussion about the role of the organisation in supporting employees to navigate ever more complex careers in a world of work that is changing faster and faster.
  • Is process good? – Many startups and high growth companies are almost firefighting with their rapid growth. Yet getting the ‘people foundations’ wrong can have huge consequences down the line as companies scale. People discussed how they can put in the right amount of process to support people career conversations without overdoing it.
  • The M word – In some organisations, the notion of a manager is almost a dirty word. Indeed many organisations are striving for flatter, more autonomous structures. What might this mean for responsibility for career conversations?

Key takeaways

The session ended with attendees noting down their key takeaway from the event. Here were some of the most popular takeaways:

  • Privileged responsibility of supporting careers – Richard’s concept about being careful of who you pass the torch to in terms of career development
  • Shared responsibility between employee and employer for career development.
  • Mindset change being needed to facilitate humble, open and vulnerable conversations.

Ultimately there isn’t a one-size-fits-all answer for how organisations can enable honest career conversations.

However, the agreement that whether you are a startup or an established corporate, enabling honest career conversations is more important than ever to retain great people.

Looking to improve career development in your company?

At GroHappy, we are helping companies to better engage and retain employees through great career development. If you’d like to hear how we’re working with other organisations and explore whether or not we can help your company, please feel free to get in touch here.

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