Nikki is a direct report of mine at work who is hilariously funny, energetic and if I were to describe her in one word: bold. She also avidly shares my belief in women sharing their experiences to support one another to succeed. I invited her (without any coercion whatsoever) to write a guest post for The Round Peg In Tweed on a topic of her choice. The only proviso being that it should be something on brand with what The Round Peg In Tweed is all about. Let me know what you think by commenting on this post; it will feed into Nikki’s performance review #kidding #butamireallykidding. 


Over the years I’ve asked a lot of people for help to get ahead. I never used to like doing it. In fact I actively resisted it. Like many of us, there’s a sense you should just be self-sufficient. Asking for help after all betrays how little you really know, especially in the workplace. Maybe it’s that intro coffee you need, a helping hand to make a deadline, insight on how to tackle a tricky manager or dear god, could SOMEONE just show me how to use Excel properly. PLEASE.

It’s never easy but I’ve gotten better at the art of the ask. Perversely, I even enjoy it. Mastery over fear of rejection is the ultimate corporate warrior’s weapon, and if you have a few skills in your arsenal you’ll rarely walk away empty handed. Here are my thoughts on how to go about it.

Have a plan – for the big ask, I go in like Napoleon. Be brave – it’s never a good time, so sometimes you have to just be bold and ask for the thing (it gets easier, I promise). Lay the groundwork and think about what you need and precisely how the other person can help you.

Create opportunities – if your target lurks making their 9th cup of tea at the kitchenette and you need something, stalk them down and catch them unawares. I’ve done my best work in lifts – people can’t escape and you’ve only got a few minutes to hook them in so it forces you to keep it short, simple and sincere.

Style up – it’s never a bad idea to rock up to a shake down looking fresh and powerful. Bust out the good blazer, shoulder pads optional.

Make it easy for people to help you – part of that is being specific about what you need. It’s easier to help someone who needs a), b) and c) by x date, than it is to just ask for “your help with this thing”. Your colleague doesn’t want to opt in for a potentially never-ending drain on their time. Whereas if it’s something quick and easy or at least with a clear end point, you will more likely get that “sure, no probs” you need.

Watch people who do it well – modelling from people who are naturally confident and don’t struggle with the ask can give you valuable insight into what style you want to cultivate, and how you might refine your approach.

Reciprocate – help should be a two way street. And even if it’s one way you can at least position it so it feels reasonable, straightforward and somehow mutually beneficial for the other person. Some people also just want to know they’ve got a favour owed back to them, which is useful in itself. Saying to someone “I really appreciate your help with this – do sing out if you ever need xyz” shows you can be of use to them in equal measure. It also shows you’ve thought about how you could help them, which is flattering (as long as it’s not condescending).

Thank with style – show your appreciation and recognition for the other person’s time and energy. Do not however abjectly weep your thank yous when successful. It’s drippy, needy and cloying – I tend to run the hell away from people who aren’t transactional and professional with their needs and thanks.

Don’t expect to be saved – even when help comes, take responsibility for the execution. It’s still your thing, you still own it. Asking for help is acceptable whereas asking to be rescued is not.

Be cheerful – dogged positivity is a hard combination to resist. Even if you get shut down, there’s a modicum of respect earned from fronting up and bouncing back. This is practicing resilience – another essential skill.

I cannot over emphasise how useful cultivating the art of the ask has come to be in my professional and personal life. When you ask someone for help you take a chance, a risk. You make yourself vulnerable, and you admit a bit of weakness. But hello – no one expects you to be an expert in everything. In admitting that you aren’t, you immediately endear yourself to people. It’s likeable as long as it’s not needy.

Your ask gives people the room to share their hard-earned know-how, which might also give them the opportunity to feel good that they are helping someone out. And that someone is 100% someone they too have been at a point in time, because we all remember how tough it is starting out.

Lastly, my ultimate tip is to try and enjoy the discomfort of the ask. You will do your best work if you can enjoy the moment, the risk and the audacity of asking for something knowing you could be refused. It’s exciting, nerve-racking and at the very worst you might be denied. But in not trying at all, you deny yourself a world of possibilities. A successful ask creates further conversation and hopefully a positive connection. Like all things, practice makes perfect.

Don’t wait for permission, or for the answer to find you. Take initiative and responsibility for getting yourself to the next step. See you out there in the big bold unknown; I’ll be asking for help right alongside you.

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