Sales Career How To’s: Promotions, imposter syndrome and changing jobs

asking for a promotion

This blog was 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]


A = Alexandra Damgaard

M = Marylou Tyler

Should you ask for a promotion?

When it comes to asking for a promotion, it’s important that your manager (or whoever you’re speaking to) doesn’t feel like it’s a conversation that’s completely out of the blue. To avoid this situation, we would recommend initiating career progression discussions with your leadership team far before you actually feel ready to take on a promotion. If you’ve just started your sales career, see our tips on how to set yourself career goals and communicate these with your managment. Once your management team knows what your long-term goals are, they’ll be much more receptive and likely to facilitate you when the time comes for your promotion.

If you’re in the position of waiting for a vacancy/ promotion to open up in your company (maybe you have to wait until your manager is either promoted or leaves), it’s really important to be incredibly proactive and communicative around the fact that you’re eager to move on to the next stage and secure that promotion when it becomes available. For example, ask management if you can start working on relevant projects with senior members of staff that will help demonstrate your readiness until that position opens up and the possibility of moving up arises. Importantly, ‘get confirmation that what you’re doing is aligned with the career path that you intend to follow.’ – M. 

So what do you do when the promotion becomes available or if you’re competing for an open position? 20% of our Women in Sales Leadership webinar audience said they’d be reluctant to put themselves forward for a promotion. So, it might be encouraging to hear that both Marylou and Alex agreed that if a vacancy arises for a position you want, then ‘Absolutely, where you can, put yourself forward and say ‘I think I’m ready to do this and I’d really like the opportunity to’ – A. Again, the more proactive you are in demonstrating your readiness before the position opens up, the more likely you will be to get it! It’s all about the prep!

Asking for a promotion and taking a proactive approach to your career progression

20% of our webinar audience said they didn’t feel prepared for a promotion due to a lack of training and preparation on the company’s behalf. If this is you, ask yourself the following questions to help you figure out if you’re really not ready or if you’re suffering from imposter syndrome. 

How are you judging your ‘readiness’ – by comparing yourself to others who have never done the job before, or to individuals who have been in leadership roles for years? When you think about this, where are you on the scale of ‘not prepared’? Has your manager told you that you’ve performed well in your current role? Have you been helping with or preparing work that’s generally the responsibility of people above you? How long have you been in your current position and what is the history of promotion-wait times for that role in your company – where are you along that scale? 

Think about your answers to those questions, and then if you still feel you’re not prepared enough, take it up with management and ask them where they feel you are in terms of your progression in the company, and what else you could do to get ready to move up.

Finally, if you’re stuck waiting for a promotion that feels like it might not happen for a long time, there are plenty of opportunities for you to branch out and start your own thing (especially in smaller companies like start-ups). If you have an interest in a leadership-based role that doesn’t exist in your current company, but that the company needs, help them see that need – create your own promotion. Some advice from a wise guest – ‘Make it about the company, show them how this new role will add to the success of their company, and that you would be happy and capable to take that on.’

‘I guess there’s always an abundance of opportunity, it’s how you view where you best fit, and you’re not going to get it right every time.’ – M

How to stop your imposter syndrome from sabotaging your career progression

It’s very common to experience nerves when putting yourself up for a promotion, and that’s okay. What’s not okay, is letting false beliefs take control or hold you back from throwing your name in the ring for a job that you’re more than capable of doing.

We know that women, more often than men, hold themselves back from going for the jobs they want because we believe that we don’t have enough experience to be considered by the hiring manager. Nevertheless, this thought process isn’t one that seems to be as prevalent in our male counterparts, who often have a ‘fail-forward attitude’ when it comes to going for jobs they are less qualified for than stipulated by the job spec. 

This self-doubting psyche is similar to ‘imposter syndrome’, something that many of our webinar guests felt they had experienced before and wanted help challenging. Imposter syndrome is that feeling of chronic self-doubt when it comes to your ability (and in the face of your own competence). Feeling like your success hasn’t been ‘legitimately achieved’. Maybe you feel like you just got lucky? Or that you’re scraping by in comparison to other colleagues who are more skilled and therefore have more of a right to be there than you (and that this will soon become apparent when you inevitably slip up). Sound familiar?

Imposter syndrome sabotaging your career progression

These feelings of doubt inhibit us when it comes to making leaps in our sales career and even in taking risks – which we know can be beneficial when it comes to success in leadership. So, what’s the answer? 

‘It’s a bit of a chicken in the egg situation right, because if you aren’t sure if you’ve got enough experience, then you’ll never go into that next role and get the experience you need… So I think that’s sort of where I’ve come out of it. If I feel like I don’t have enough experience, that’s okay to begin with. If I need support on the way I can reach out to other people for guidance, and that doesn’t mean that I’m not capable of the role, it just means that I’m self-aware and responsible enough towards my duties to make sure that I get the support I need.’ – A

The steps we can take to shed our imposter syndrome

  1. Ask for feedback. ‘When you’re doubting yourself, other people telling you that you’re doing a good job can be quite a good medicine. So, if you’re not receiving feedback from your manager or your peers, then I’d say, asking for feedback is a good first step. I think that can really help to just boost your confidence a bit and prove, with some external validation, that you are doing a good job.’ – A
  2. Try to minimise the impact of your perfectionism. There is a strong link between ‘perfectionism’ and imposter syndrome. Why? The unrealistic standards and expectations set by perfectionists are often unobtainable. Producing perfect work 24/7 is unrealistic (especially in the modern work environment where we’re expected to produce a huge volume of work), and therefore if you’re always striving to be the best of the best, you’re inevitably setting yourself up for failure. Feeling like you’ve failed, or that your work is sub-par compared to others, initiates that imposter syndrome feeling and the cycle goes on. So, it’s okay to set high standards for yourself, but try to make them realistic – no one can do everything perfectly. If you struggle with perfectionism, here is a helpful article that might help you figure out when ‘good is good enough’ and put down your work. 
  3. If you’re struggling to have confidence in your ability to do the job, try and have confidence in your ability to learn on the job – where messing up and failing play a huge role. Remember that no one is supposed to know everything the moment they step into a new role (or even a few years down the line).
  4. Ask for help from your network and colleagues when you need support. This doesn’t invalidate your ability to do the role, it only confirms your commitment to doing it well.
  5. Celebrate every little win, and acknowledge the part you played to make that happen.
  6. Try to minimise the amount of attention you pay to the negative influences (or people) in your life that are telling you that you can’t do it. ‘It’s very hard, we all have insecurities about our self-worth. You have to get rid of these negative influences and give yourself permission that you can get to where you want to go.’ – M
  7. Making constant upwards comparisons can be really detrimental to how we view our own ability. As the saying goes ‘comparison is the thief of joy’. Those with imposter syndrome tend to exclusively compare themselves upwards and to those around them such as senior employees who are seemingly excelling at their job 24/7. If you catch yourself doing this, try to reassess who you’re comparing yourself to. Try to compare yourself to the peers within your own cohort, and recognise that there are probably colleagues in your team who actually look up and compare themselves to you. 
  8. Ask yourself what’s the worst that can happen and then ‘throw your ego in your pocket’. ‘We used to have a saying with Predictable Revenue – Don’t worry be Crappy. And really, that’s truly the path of enlightenment, especially in sales’ – M. 

Don’t be too afraid to move around

Moving company does not have to be at a detriment to your career progression, in fact, it may be quite the opposite. 

If you’re in the position of having to wait for a vacancy to open up before you can move into a more senior role, it is certainly worth looking to see whether that opportunity is available elsewhere. As well as potentially fast-tracking your promotion, stepping into a leadership role as an outsider gives you the opportunity to go in as that senior person and to leave any preconceived notions that might have existed about your ability in your previous company. 

Moving into a new company

‘As much as you might love working there … moving company can be a good thing, it can give you that opportunity to come into a more senior role as that senior person, without having to feel like you have any history of not being that senior person if that makes sense … It helped me, because I could then really present myself to this other company as a leader, and that that’s what I was there to do and to be.’ – A

However, depending on your industry it may not be wise to jump ship too many times. 

So, how do you know when it’s the right time to move? 

  1. Be cognizant of your industry

‘It’s not going to hurt you to move around in certain industries, but you have to be cognizant of your industry … for example, insurance companies [in the US], have preconceived assumptions that you’re a non-performer if they see you’ve moved around too much. So work within your boundaries when it comes to moving around companies … In sales, we do have certain thresholds that we’re looking for when it comes to how long we want you to be in certain roles, and again that will change depending on the company and industry you’re in. So, you’re gonna have to sort of test the waters when you get in there.’ – M

It’s useful to know how long you should expect to stay in a role within each industry. In the Tech and SaaS world, the number of months you’re expected to stay within a role like the sales development role is typically shorter than in industries like Life Sciences. Nevertheless, that time-frame again depends on how complex the Tech you’re selling is, and how well the company wants you to know it before you move up. So use your internal network and do your research. If you’ve been in the same role for longer than the usual time-frame and you’re stuck waiting for a promotion that doesn’t look like it’s opening up any time soon, then no one would blame you for looking elsewhere.

Generally, if every move you’ve taken has shown you’re moving in a clear career trajectory, resulted in a better job or a better company, it’s more likely to be used in your favour than it is to be used against you. But, pe prepared to explain exactly why you left each job in an interview, and make sure to link it back to personal development reasons.

  1. Are the benefits going to outweigh the costs?

Once you know the above, it’s easier to work out how much moving may ‘cost you’ in terms of reputation (which is obviously industry dependent). It’s then time to weigh out what the benefits are. Perhaps your new job has given you the opportunity to step into a leadership role? Maybe it was benefits like flexible working hours that enticed you to move – read more about the impact coronavirus has had on flexible working, work-life balance and how to manage it here. Or perhaps it’s a company that will help you side-step into a different part of the industry entirely. 

‘When I got into the working world, I must admit I chased the money. I was looking to figure out how I could hop, you know, catapult myself into positions. I wasn’t worried about tenure. I wasn’t worried about anything to do with longevity, I didn’t understand how it all worked and whether it was important, or not. I moved where the opportunity was, knowing that I had just enough of the expertise that was needed, and then I could figure out the rest, because as an engineer, that’s what we do, we’re trying to solve problems all the time, so we don’t know the answers all the time. And that was okay with me. I wasn’t necessarily worried about fulfilling the other part of my legacy which was becoming an expert in my field. That was so far removed, I never really thought about that. But it soon became the other way around.’ – M.

Finally, if the only reason you’re considering moving job is your salary, we ask you this. Other than taking issue with your pay, are you happy with your job and the company you work for? 57% of women say they’ve never negotiated with an employer over pay, but 60% say they’ll leave an employer to get a salary bump somewhere else, which means more women would rather leave their job than negotiate their salary. Contrary to this statistic, we think that if you’re happy with where you are, it’s definitely worth trying to re-negotiate your pay with your current employer before moving. Learn how to re-negotiate your salary here.

To summarise, how long you intend to stay at a company or in a role should fluctuate depending on what you need from your career at the time and jumping around doesn’t have to be detrimental to your career if you make industry-specific decisions that are right for you.


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