This blog was hugely inspired by the advice given by Marylou Tyler, co-founder of Strategic Pipeline and Alexandra Damgaard, co-founder of Sales Impact Academy, at the ‘Women in Sales Leadership’ webinar we hosted on the 4th of November. If you’d like the recording, please email: [email protected]
Quotes:
A = Alexandra Damgaard
M = Marylou Tyler
‘This is your career, right, your career. So you’re the one who’s going to decide the path you want to take, or at least get to that next step’ – M
1. Set yourself goals
There’s two ways to know if you’re going down the right career path:
Number 1 – If you’re enjoying it. Number 2 – If you know where you want to end up.
This sounds obvious, yet so few people actually make and/or consistently re-evaluate their career goals. Why is this important? It’s a lot easier to make informed and correct decisions about your career when you know where you want to go with it.
So, when you’re setting career goals, you need to ask yourself, ‘based on my experience, my likes and dislikes, do I think I’m going to enjoy it?’ If the answer is yes, you can start to set your three goals. ‘What’s my marginally acceptable goal? What is the goal that I would love to achieve, and what’s my woopy (or stretch) goal?’ – M. Sometimes, it’s easier to start small and keep it short-term. Especially when you’re at the beginning of your career as this leaves more room for error and time for us to re-evaluate – many of us don’t get it right the first time. For example, if you don’t know where you want to be in 5 years, that’s okay. Just focus on what you’re enjoying at work – see tip 2.
On the other hand, if you know exactly where you want to go and have a fittingly ambitious stretch goal – maybe you want to be the VP of Sales? – it can be easy to feel overwhelmed when you’re considering how you’re actually going to get there. To combat this, you need to plan and break that down. Focus specifically on what you can do to get to the next step, and socialise that. By this we mean, start working towards that short-term goal and communicate with your manager or leadership team. Tell them what you want, and ask them how you can prepare to take the next step (whether that be a promotion or moving to a slightly different role). By doing this you’re showing them that you’re ambitious, proactive and keen to learn, and as a result, they’ll be much more likely to put you up for the internal opportunities you need to thrive.
Finally, remember to celebrate the little wins. ‘It’s the little wins that help squelch that uncertainty and doubt that you may have in your ability. The more … you get along the way, the more your confidence will grow’ and the closer you’ll feel to reaching your big goal – M

2. Be Proactive when it comes to your career progression
In every step of your sales career, try to be as proactive as you can. Take the first step, don’t wait for others to do things for you, initiate ideas and business plans, advocate for yourself, ask to take on challenging projects, look to for opportunities to demonstrate your abilities and take advantage of the opportunity’s thrown your way. This style of behaviour – putting yourself out there in such a candid way – can be quite a tricky thing to get used to. Especially in the early years of your career when you feel like the least qualified member of the room. Moreover, having a path planned for out us at school and university does not always prepare us well for the onus we’re required to take when it comes to our own career progression. So, unsurprisingly it can be quite a difficult transition. Nevertheless, Alex’s quote nicely illustrates the effect proactivity had in the early stages of her career.
“Reflecting back on my career, one of the main things I remember is that I started off quite passive. I’ve never really known what I wanted to do, or what I wanted to become. I’ve never been one of those people who have a 5-year or a 10-year plan. And I think, to begin with, I was quite naive. I sort of sat back and expected my company to provide me with all the training I would need, to guide me straight into my next role and that my career path would just have this mapped journey that I would follow naturally. That is not the case. You know, my first manager sat me down and said ‘One of the main things you need to know about working here is that you need to own your career progression because no one else is going to do it for you’ … So, you need to be asking for things. You need to be asking to work on projects, you need to be telling your manager when you want to be promoted or that you want to be promoted, and what it is that you’re interested in. You want to be more of a people manager? Okay, so how are we going to get you there? Owning your career, even if you don’t know where you want to be. Knowing which areas you’d like to develop (for me it was people management), then really asking for what you want. That was, I’d say, the main thing that’s really shaped my career. Just asking for it.” – A

So, as you can see even without a clear long-term career progression plan, it’s more than possible to be proactive when it comes to your career development. You just have to focus on developing the skills that you enjoy or as Marylou says ‘Follow your strengths’. Pro-activity is the string that ties this blog together and because of that we can’t emphasise enough the impact that this kind of attitude can have on your career success.
‘Be proactive in seeking out what you need in order to thrive, and I promise you will get there’ – M
3. Network and engage with your industry community
Networking and engaging with the industry community can you help you in a variety of of ways, including the following four:
Joining industry-specific community groups – such as private forums on LinkedIn – is an easy way to engage with individuals who have similar work-interests to you. As well as providing you with access to peers who can understand the work-related highs and lows you’re going through, an industry-related group can also be a source of untapped and free educational information. When you’re searching for groups to join, look for communities with active members who are posting articles, courses and events that are hyper-relevant to you. You don’t want to spend hours scrolling through, only to find one piece of content that’s worth reading or signing up for. Something else to consider, joining groups with active industry leaders. This will provide you with an opportunity to learn from those you admire in the industry, and it will provide you with a topic of discussion if you ever want to reach out to them. Finally, don’t forget to give back to the community! The more you engage, the more others will engage with you.
Aligning yourself with a community of people in a similar field or industry can prove very lucrative when it comes to job-hunting. The more industry-related groups and people you have relationships with, the more likely you are to be informed of new job opportunities. But, don’t forget to nurture the connections you do have, especially your close ones. It will help keep you top of mind when it comes to others considering you for job opportunities.
Networking can also be a great way to understand and explore the different career paths people have chosen to take in an industry. For example, if you know you want to get into sales leadership, look for opportunities to start conversations with people in those positions. Ask them where they started, the challenges they faced, how long they waited to move between companies etc. At the minimum, have a conversation at lunch with your more experienced colleagues. Get some intel as to what an upward mobility path looks like within your company based on how your senior colleagues have progressed through, and whether you’d feel comfortable following a similar path. Second to that, use LinkedIn! Look at how sales leaders in your field have moved through their career. Take inspiration and use it to inform decisions such as how long you should expect to stay put in your current role and based on that, when you could start discussing preparing for a promotion with your manager.

Finally, try to develop a close network of people you can trust – think your closest colleagues or a mentor. A network like this brings an element of safety when it comes to sharing things such as things that are causing you to doubt your ability, or issues with management at work. Often the more you share, the better you feel because you end up hearing ‘the same thing happened to me’. ‘When you start hearing that, it lessens the importance of whatever thing is keeping you down … That’s the beauty of having a community around you, having peers and colleagues with whom you can have conversations like this. It helps minimise the importance that your psyche is placing on whatever that thing is.’ – M
4. Find a mentor
‘I mean 35 years I’ve been doing this. Doing it right, doing it wrong, doing it sideways and upside down. I have a lot of things to share, and I would love to do that.’ – M
The benefits of mentorship are abundant – read more in our blog Mentors, Sponsors and Coaches: The key to your career succeess. Who wouldn’t want an experienced adviser to confide in and seek advice from? Perhaps, to even work with and feature in a webinar you’re hosting? So, unsurprisingly, a lot of people asked about mentorship and how to find a mentor! Here’s some advice from Marylou:
‘We all want to help in a variety of ways. But we’re not going to be proactive and reach out to you for that help, it’s the other way around. So, if you’re not where you want to be, there are folks, mentors, helpers that are along that spectrum of expertise (in leadership, or whatever it is you’re interested in), who can help guide you along this path. You just have to reach out and ask for assistance. I think you’ll be pleasantly surprised. I always say this but my phone number and my email address are on my website. Can I tell you how many people have actually called me of the thousands of people that I talk to all the time. It’s a very small percentage.’
Trying to connect with people can be scary, mostly because the thought of being rejected is scary. In this instance however, you have to put your ‘ego in the pocket and make that call’ – M. The worst that’s going to happen is they say no. On the other hand, if your call or message goes well, and you make that connection, you could form an extremely valuable relationship that may benefit you hugely in your sales career. So, put plainly, the benefits far outweigh the potential con’s.
‘The more proactive that you are in seeking assistance and advice and guidance, the more successful you will be, which will also build your confidence.’ – M
If you’d like a free list of groups that help women in sales to find experienced mentors, blogs, podcasts, industry communities to follow and more, download our free resource here. Curated specifically to address the challenges presented to us by the attendees of our women in sales leadership event.
By, JT