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You can only take your business so far without hiring other experts as leaders. Sometimes a certain team may grow and they may require their own leader. How do you know when that new leader is needed? 

It’s important to show appreciation to those who got you this far but it’s also important to know when new blood is needed as an addition to your business.

Dynamic Business asked experts when they know it’s time to grow their leadership team?


Michelle Sales, author of The Power of Real Confidence:

What got us here won’t get us there’ is true for leaders as much as it is for leadership teams. As a leader, reflecting on your team, it’s purpose, it’s performance and it’s ability to step up and respond to both current and future demands is critical. You often need to lead differently tomorrow from how you lead today. Investing in the growth of leadership teams is an ongoing process. Not something that happens once or twice a year. Growth as a mindset as much as a capability is important for team performance. More than ever, leaders are expected to inspire their teams through worlds of complexity and uncertainty, to unite them, and give them drive and great purpose. Stepping up and leading this is real growth.

Scott Stein, author of Leadership Hacks, leadership specialist:

When workload becomes too much for you and your direct reports it’s time to look at expanding your leadership team.  When tasks increase beyond current capacity mistakes start occurring and results can suffer.  If you and your people are functioning at a high level of performance and not able to keep up, bringing an additional team member that can add a fresh level of perspective, additional skills and additional experience in getting things done.  The biggest challenge that I notice is that too many leaders wait too long to bring in this resource—people get exhausted and opportunities can be missed.MITCH LAWSON

Mitch Lawson, Chief Marketing Officer, TRAVLR & The Bali Bible:

This is a tough one and it’ll depend on your current team and business. At TRAVLR we’ve invested early in a strong, experienced leadership team with vast experience across start up and mature business to ensure we’re set up for success from the start.

Adam Theobald, Founder, Ordermentum & Hey You:

You know it’s time to grow the leadership team when you start to see signs of misalignment. This can take many different forms depending on the business. Key signs are when people start to become unclear on what the business’s current focus is, to noticing when people across different teams begin to find it more difficult to work together.Another big red flag is when strategy and operations discussions start to blend into one; your leadership team is there to ensure resources are in the right place to meet the business objectives. While wrestling the crazy founder or founders (sometimes) out of the way is certainly no small feat, it’s extremely important to recruit and promote smart leaders with great established experience and awesome domain knowledge to up-skill the business. They should have a strong sympathy for the challenges and differences that come in the startup / challenger world. Hiring a head of people, and establishing a leadership team to separate operations and strategy responsibilities was a crucial phase in both Ordermentum and Hey You (formerly Beat the Q). Our chairman once made a very specific request of my Co-CEO / co-founder and I; he wanted us to work on the business, not in it. This will continue to resonate with the both of us.

Yanir Yakutiel, founder and CEO, Lumi: 
For me the cue is when the existing team getting into a group think mode. We all work very hard and are committed to the same goals, so over time it’s quite easy to conform to the group thinking. At that point I always feel it’s a good idea to add someone new to the team to refresh the thinking. One of the most common mistake leaders make is to surround themselves with clones of themselves who complement their strengths. You should do the opposite – surround yourself with people who complement your weaknesses and empower them.

Aaron McEwan, HR Advisory Leader, Gartner:

The best organisations balance their leadership bench in response to, or anticipation of, what they need to achieve. This concept places a heavier focus on ensuring that we have the right leaders deployed against the right things.

Organisations should look to get the right leaders into the right roles to drive the right outcomes. This means establishing the leadership team necessary to support the organisation’s strategy. If the strategy is to grow, then form the leadership team that will drive growth. Smart organisations do this ahead of the growth curve as opposed to waiting for signs of growth before investing in talent.

While this does mean rethinking our traditional static approaches to leadership, being responsive top changes in the market, and investing ahead of growth encourages greater agility, innovation, and, ultimately, higher performance.

Stephanie Christopher, CEO, The Executive Connection:

Leaders are supposed to be the change agents in every business. When an organisation stops transforming, innovating and moving forward, then it’s time to consider injecting some fresh ideas and perspectives.

Data from The Executive Connection’s Customer Growth Report shows that businesses who nurture dedicated leadership across business functions, such as sales or marketing, have the ability to achieve consistent growth and stay one step ahead of competitors; the ultimate business goal.

As we approach the end of the year, now is the ideal time for CEOs and business owners to take stock and determine if enhancing capability across the leadership team will help the drive long-term results.

Jake Colvin, Co-founder and Director of International Operations, Owlet:

As any founder or entrepreneur can attest, you wear a million different hats to get the job done – particularly in the early days. For this reason, you can easily be overloaded with work and feeling extremely stretched, before it dawns on you that it’s time to expand your leadership team.

It can be a difficult task because it means stepping back and letting others take ownership of specific roles and responsibilities. But it also allows you to focus in on your strengths,  to grow the business more than ever before.

For Owlet, we knew it was time to grow our leadership team when our revenue and headcount nearly doubled, and we began looking to expand into new geographies. To be successful in this next stage of our business, we had to dedicate extra firepower to them. It made sense to bring experts from these areas on board to navigate the challenges of rapidly expanding our business in different regions.

That said, we’re also heavily focused on fostering internal leadership and building talent within our business. Good people are the foundation of any successful start-up or small business, so it’s essential to spend time instilling leadership skills and values among your employees and to always set a good example by how you lead.

Nicole Gorton, Director, Robert Half Australia:

The modern workplace is a busy and everchanging environment. With increased pressure from competitors and faster methods of communication, the demands on business leaders to make the right decisions have never been more apparent. Keeping pace with market demands sometimes means having to grow your team, or better yet, your leadership team. How do you know it’s time? Key indicators to look for include:

1. If you’ve gone through a steady increase in business growth and need more senior level support

2. If you require more experienced or a specialised skill sets

3. If you need more managerial oversight

4. If you’re struggling to make time for your team’s personal development

While its beneficial to look externally for new leadership talent that will help you deliver a competitive edge, you should also assess the team you have around you. Better yet, be anticipatory. Create a leadership development program for your staff, which will help them develop the skills they need to move up within your organisation and grow professionally. While these programs can take time to build, they can generate help your employees feel more connected to the business, and understand how their work adds value.

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Gali Blacher

Gali Blacher

Gali Blacher, editor, Dynamic Business

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