
Sandy MacDonald
President of the Holland College
1
APPEARANCES
1
PODCASTS
012
DEC 30
JAN 6
JAN 13
JAN 20
JAN 27
FEB 3
FEB 10
FEB 17
FEB 24
MAR 3
MAR 10
MAR 17
MAR 24
MAR 31
APR 7
APR 14
APR 21
APR 28
MAY 5
MAY 12
MAY 19
MAY 26
JUN 2
JUN 9
JUN 16
JUN 23
JUN 30
JUL 7
JUL 14
JUL 21
JUL 28
AUG 4
AUG 11
AUG 18
AUG 25
SEP 1
SEP 8
SEP 15
SEP 22
SEP 29
OCT 6
OCT 13
OCT 20
OCT 27
NOV 3
NOV 10
NOV 17
NOV 24
DEC 1
DEC 8
DEC 15
DEC 22
DEC 29
JAN 5
JAN 12
JAN 19
JAN 26
FEB 2
FEB 9
FEB 16
FEB 23
MAR 2
MAR 9
MAR 16
MAR 23
MAR 30
APR 6
APR 13
APR 20
APR 27
MAY 4
MAY 11
MAY 18
MAY 25
JUN 1
JUN 8
JUN 15
JUN 22
JUN 29
JUL 6
JUL 13
JUL 20
JUL 27
AUG 3
AUG 10
AUG 17
AUG 24
AUG 31
SEP 7
SEP 14
SEP 21
SEP 28
OCT 5
OCT 12
OCT 19
Jun 7, 2026
The Best Skills Lawyers Can Learn NOW
21:58
22:06
22:13
22:20
22:36
22:52
25:59

Holly CopeHOST
In this episode, I'm interviewing Sandy McDonnell, senior director and head of legal operations at DocuSign.

Sandy MacDonaldGUEST
The people that will be replaced are the people that aren't using AI, right? The people who are unwilling to adopt.

Sandy MacDonaldGUEST
So for me, it's really been finding really narrow use cases, like understanding what individual people's pain points are.

Sandy MacDonaldGUEST
Like not even necessarily like a function, like really going to an individual person kind of level and helping them see, okay, how can AI help me in me- in my job, in my day-to-day work? We have this idea of like legal as the builder, which I think is really exciting.

Sandy MacDonaldGUEST
And it, you know, I think we went from like IT was always the, the, the builder and, and implementer of technology, and then legal ops was, and like I love when I can build out my own workflows and create my own custom extractions and, and whatever.

Sandy MacDonaldGUEST
Like I have folks on my le- my broader legal team who are like building their own agents, right? And I think that is so cool.

Holly CopeHOST
And it's like, well, if you compare that with a human, a human wouldn't be able to do that, so why are you expecting that? [laughs]